WO1999010317A1

WO1999010317A1 - Biarylalkylenecarbamic acid derivatives and bacteriocides for agricultural and horticultural use

Info

Publication number: WO1999010317A1
Application number: PCT/JP1998/003736
Authority: WO
Inventors: Kazuhiro Ikegaya; Masami Ozaki; Takahiro Kawashima; Ichiro Miura; Norimichi Muramatsu
Original assignee: Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.
Priority date: 1997-08-26
Filing date: 1998-08-24
Publication date: 1999-03-04
Also published as: ATE292112T1; DE69829574T2; US6620961B1; AU8749598A; DE69829574D1; BR9814789A; EP1010690A4; EP1010690B1; EP1010690A1

Abstract

Biarylalkylenecarbamic acid derivatives represented by general formula [I] and bacteriocides for agricultural and horticultural use, wherein Q is optionally substituted phenyl or the like; X is halogeno, C1-C6 alkyl or the like; n is an integer of 0 to 4; R1 is C1-C6 alkyl or the like; R2 is hydrogen, C¿1?-C6 alkyl or the like; A is optionally branched C1-C7 alkylene; and G is oxygen, sulfur or -NR?3¿- (wherein R3 is hydrogen or C¿1?-C4 alkyl). The bacteriocides not only exhibit a high control effect against cucumber downy mildew, apple scab, wheat powdery mildew, rice blast, cucumber gray mold and rice sheath blight, but also are characterized by causing no chemical damage to crop plants and being excellent in residual effect and rain resistance.

Description

Biarylalkylenecarpa'minic acid derivatives and agricultural and horticultural fungicides

Technical field

The present invention relates to a novel biarylalkylene carbamic acid derivative and a fungicide for agricultural and horticultural use containing the derivative as an active ingredient.

Background art

Conventionally, many carbamic acid derivatives have been reported, but it is not known that the biarylalkylene-potency rubamic acid derivative of the compound of the present invention has an excellent bactericidal action.

The present inventors have conducted intensive studies to create a novel agricultural and horticultural fungicide. In addition, the present invention has been found to exhibit a remarkable effect as an agricultural and horticultural fungicide, leading to the present invention.

Disclosure of the invention

That is, the present invention provides a compound represented by the general formula [I]:

{Wherein, X is a halogen atom, (C 1 one C ₆₎ alkyl groups, (C - C ₆₎ alkoxy groups, (C i- C 4) haloalkyl group or; - a (C C 4) haloalkoxy group And n represents 0 or an integer of 1 to 4, R 1 represents a (C—C ₆ ) alkyl group,

A (C 2 -C 6) alkenyl group, a (C 2 -C ₆ ) alkynyl group, a (C ₃ -C ₆ ) cycloalkyl group or a (C i -C ₄ ) haloalkyl group, wherein R ² is a hydrogen atom,

(C 1- C ₆₎ alkyl groups, (C 2- C ₆₎ alkenyl, (C 2- C 6) al Kiniru groups, (C 1- C 4) alkoxy groups, (C - C 6) alkoxy Guji E One C ₄ ) alkyl group, (C i — C ₆ ) alkylthio (C j — C ₄ ) alkyl group,

(C! -C4) haloalkyl group, (Ci-Cs) alkylcarbonyl group, fenii Carbonyl group, (C i -C ₄ ) alkoxycarbonyl group or aryl (C i -C 4) alkyl group [this group is a halogen atom, (C 丄 -C ₃ ) alkyl group, (C -C ₃ ) ) It may be substituted by an alkoxy group. A represents an optionally branched (C 1 -C ₇ ) alkylene group, G represents an oxygen atom, a sulfur atom or a group NR ³¹ [R represents a hydrogen atom or (C i — C ₄ ) Represents an alkyl group. ] And Q is a general formula

[A-1] represents a group represented by [A-2] [A-3], in which Y is a halogen atom, nitro, cyano, hydroxy, (C 丄 —C ₆ ) alkyl group, C 2- C ₆₎ alkenyl, (C ₂ - C ₆₎ alkynyl, (C 3- C 6) cycloalkyl group, (C 3- C 6) cycloalkyl Le (C 1 one C 4) alkyl group, ( C 1 one C 6) alkoxy _{_{groups, (C 2 - C 6)}} 7 Rukeniruokishi groups, (C 2- C 6) Arukiniruokishi group, (3- C 6) cycloalkyl alkoxy, (C丄- C ₆₎ alkylthio Group, (C 1 -C ₆ ) alkylsulfinyl group, (C 1 -C 6) alkylsulfonyl group, (C i -C 4) alkoxy

(C -! C ₄₎ alkyl groups, (C i-C ₄₎ alkylthio (C i- C 4) alkyl Le group, (C丄one C 4) haloalkyl group, (C丄-C 4) haloalkoxy group,

(C1-CA) haloalkylthio group, (Ci-C4) haloalkylsulfinyl group, (C1-C4) haloalkylsulfonyl group, (C-C4) alkylcarbonyl group, (C1-1C4) The alkoxycarbonyl group and the group CONR ⁴ R ³ [R ⁴ and R ⁵ are the same or different and represent a hydrogen atom or a (C i -C ₄ ) alkyl group. ], Amino group, mono (C-1C4) alkylamino group, di (C-1C4) alkylamino group,, (C1-C4) alkylcarbonylamino group, aryl group

[Said group halogen atom may be substituted by (C i- C 4) alkyl or (C i-C ₄₎ an alkoxy group. ], Aryloxy group [the group is a halogen atom,

(C -! C ₄₎ alkyl or (C i- C ₄₎ may be substituted with an alkoxy group. ], Aryl (C 11 -C) alkoxy group [the group is a halogen atom, (C 1 — It may be substituted by a C 4) alkyl group or a (CCC 4) alkoxy group. Or an adjacent substituent may be bonded to form a methylenedioxy group, and m represents 0 or an integer of 1 to 5. and a fungicide for agricultural and horticultural use containing these as an active ingredient.

The symbols and terms described in this specification will be described.

A halogen atom is a fluorine, chlorine, bromine or iodine atom. (C -! C ₆₎ notation, etc., the number of carbon atoms of the substituent following this have shown that in this case is 1-6.

The (C 1 -C ₆ ) alkyl group means a linear or branched alkyl group, for example, methyl, ethyl, η-propyl, isopropyl, η-butyl, isobutyl, sec-butyl, tert-butyl , N-pentyl, isopentyl, neopentyl, n-hexyl, 3,3-dimethylbutyl and the like.

The (C3-C6) cycloalkyl group includes, for example, cyclopropyl, cyclopentyl, cyclohexyl and the like.

(C 1 -C 4) haloalkyl group means a linear or branched alkyl group substituted by a halogen atom, such as fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, Fluoroethyl and the like.

(C 2 -C ₆ ) alkenyl group means a linear or branched alkenyl group, for example, vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2- Butenyl and the like.

(C 2 -C ₆ ) alkynyl group means a linear or branched alkynyl group such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 4 -Methyl-1-pentynyl, 3-methyl-1-pentynyl and the like.

The (C 1 -C 6) alkoxy group refers to an alkyloxy group in which the alkyl portion has the above-mentioned meaning.

The (C 2 -C ₆ ) alkenyloxy group refers to an alkenyloxy group in which the alkenyl moiety has the above-mentioned meaning. The (C 2 -C 6) alkynyloxy group refers to an alkynyloxy group in which the alkynyl moiety has the above-mentioned meaning.

The (C 3 -C 6) cycloalkoxy group indicates a cycloalkyloxy group in which the cycloalkyl group part has the above-mentioned meaning.

The (C! -C ₄ ) haloalkoxy group is a haloalkyloxy group in which the haloalkyl moiety has the above-mentioned meaning.

The (C! -C ₆ ) alkylthio group refers to an alkylthio group in which the alkyl portion has the above-mentioned meaning.

The (C 1 -C ₆ ) alkylsulfinyl group refers to an alkylsulfinyl group in which the alkyl portion has the above-mentioned meaning.

The (C 1 -C β) alkylsulfonyl group refers to an alkylsulfonyl group in which the alkyl portion has the above-mentioned meaning.

The (C 1 -C 4) haloalkylthio group refers to a haloalkylthio group in which the haloalkyl moiety has the above-mentioned meaning.

(C 1 -C 4) haloalkylsulfinyl group means a haloalkylsulfinyl group in which the haloalkyl moiety has the above-mentioned meaning.

(C 1 -C 4) haloalkylsulfonyl group means a haloalkylsulfonyl group in which the haloalkyl moiety has the above-mentioned meaning.

An optionally branched (C i—C?) Alkylene group is, for example, one CH ₂ —, one CH (CH 3) one, one C (CH 3) 2 —, one CH 2 CH 2 —, one CH ₂ CH ₂ CH ₂ — and the like.

The aryl group refers to phenyl, 1-naphthyl, 1-naphthyl and the like.

Aryl (C-C4) alkyl group means benzyl and the like.

The aryloxy group refers to phenoxy, naphthoxy and the like.

Aryl (C 丄 —C 4) alkoxy means benzyloxy or the like.

Next, specific examples of the compound of the present invention represented by the general formula [I] are shown in Tables 1 to 53. However, the compound of the present invention is not limited to these compounds. The compound number is referred to in the following description. (table 1 )

(Table 2)

(Table 3)

(Table 4)

Compound ΪΠΙ G Ri R Melting point

(° C)

1-80 4-SO2CH3 0 CH ₃ H

1-81 3-CH2SCH3 0 CH ₃ H

4-CH2SCH3 0 CH ₃ H

丄-d-Ui 20 0 CH ₃ H

1

丄-84 4-LHi ^ 0 CH ₃ H

1 ο

l-oo 3-SOCHF2 0 CH ₃ H

1-86 4-S0CHF 0 CH ₃ H

1-87 3-SCF3 0 CH ₃ H

1-88 4 H 0 CH ₃ H

1-89 3-SOCF3 0 CH ₃ H

1

1-90 4-SOCF3 0 CH ₃ H

1 1

1-91 3- S0 ₂ CF ₃ 0 CH ₃ H

1 no

4-SO2CF3 0 CH ₃ H

1-93 3-C0CH3 0 CH3 H 92-93

1-94 4-C0CH3 0 CH ₃ H 103-104

1 π

1-95 3-COOCH3 0 CH ₃ H

1-96 4-COOCH3 0 CH ₃ H

iy d—Shi u u CH ₃ H

1-98 4-COOC2H5 0 CH ₃ H

1-99 3-C0 H2 0 CH ₃ H

1 1

丄-丄 ϋϋ 4-ϋ thigh 2 u CH ₃ H

1-Ιϋΐ -CON (CH3) 2 0 CH ₃ H

1-Ιϋώ 4-LUl (U) 2 u CH ₃ H

1-lUo J- 02 0 CH ₃ H 79-82

1-104 4-N0 ₂ 0 CH ₃ H

1-105 3-C 0 CH ₃ H

1-106 4-CN 0 CH ₃ H

1-107 3- H ₂ 0 CH ₃ H

1-108 4-NH ₂ 0 CH ₃ H

1-109 3-NHCH3 0 CH ₃ H

1-110 4-NHCH3 0 CH ₃ H

1-111 3-N (CH ₃ ) ₂ 0 CH ₃ H (Table 5)

_Π 1

Compound O Yra GR ¹ R Melting point c)

1-112 4-N (CH ₃ ) ₂ 0 CH ₃ H

1-113 3-NHCOCH3 0 CH ₃ H

1-114 4-NHCOCHQ 0 CH ₃ H

_{_{1-115 3-NHC0C 2 H 5 0}} CH 3 H

_{_{1-116 4- HC0C 2 H 5 0 CH}} 3 H

1-117 2, 4-Cl ₂ 0 CH ₃ H 77-80

1-118 0 CH3 H Oily substance

1-119 3, 5-Cl ₂ 0 CH ₃ H Oil

1-120 3, 4-F ₂ 0 CH ₃ H 40-43

1-121 3, 5- F ₂ 0 CH ₃ H

1-122 3-CI, 4- F 0 CH ₃ H 60-61

1-123 2, 4- (CH ₃ ) ₂ 0 CH ₃ H

1-124 3.5- (CH ₃ ) ₂ 0 CH3 H

1-125 3, 4- (CH ₃ ) ₂ 0 CH ₃ H Oily substance

1-126 2, 4- (OCH3) 2 0 CH ₃ H

1-127 3, 4- (0CH ₃ ) ₂ 0 CH ₃ H

1 1 o 3, 5- (OCH3) 2 0 CH ₃ H

1-1 9 3-F, 4-CH3 0 CH ₃ H

1: ί0 3- CI, 4-CH3 0 CH ₃ H

1-131 3-CH3, 4-F 0 CH ₃ H

1-132 3-CH3, 4- CI 0 CH ₃ H

1-133 3-CH3, 4- Br 0 CH ₃ H

1-134 4-Cl, 3-OCH3 0 CH ₃ H

i-4-Cl, 3-0C ₂ H ₅ 0 CH ₃ H

1-136 3, 5-(CH ₃ ) ₂ , 4-F 0 CH ₃ H

_{1 - 137 3-N0 2,} 4-CH3 0 CH 3 H 82-83

1-138 3, 5- (CF ₃ ) ₂ 0 CH ₃ H

1-139 2, 4- (CF ₃ ) ₂₀ CH ₃ H

1-140 2-OCH3, 5-Br 0 CH ₃ H

1-141 2-F, 4-CF3 0 CH ₃ H

1-142 3, 4- (0CH ₂ 0) 0 CH ₃ H

1-143 3, 4, 5-CI3 0 CH ₃ H (Table 6)

Compound Ym G R R Melting point

(° C)

1-144 3, 5- F2, 4-C1 0 CH ₃ H

1-145 2, 4, 6- (C¾) 3 0 CH ₃ H 89-91

1-146 H 0 C2H5 H Oil

1-147 H 0 3H7 H Oil

1-148 H 0

H oil :)

1-149 H 0 C5H1 1 H

1-150 H 0 C3H7- i H 61 64

1-151 H 0 H

1-152 H 0 (¾C CH H

1-153 H 0-<J H

1-154 3-CH ₃ 0 H

1-155 4-CH3 0 1 H

1-156 H 0 \ H

1-157 H 0 CH2C1 H

1-158 3-CH3 0 CH2C1 H

1-159 4-CH3 0 CH2C1 H

1-160 H 0 CH ₂ CF ₃ H

1-161 3-H3 0 CH ₂ CF ₃ H

1-162 4-CH3 0 CH ₂ CF ₃ H

1-163 H 0 CH ₃ CH ₃ oily material

1-164 H 0 ¾ ^H 5 CH ₃

1-165 H 0 CH ₃ C2H5 oil

1-166 H 0 CH ₃ C3H7 oil

1-167 H 0 CH ₃ C4H9

1-168 H 0 CH ₃ CH ₂ CH = CH ₂ oily material

1-169 3-CH3 0 CH ₃ CH ₂ CH = CH ₂

1-170 4-H3 0 CH ₃ CH ₂ CH = CH ₂

1-171 3-F 0 H ₃ CH ₂ CH = CH ₂

1-172 4-F 0 CH ₃ CH ₂ CH = CH ₂

1-173 2-CI 0 CH ₃ CH ₂ CH = CH ₂

1-174 3- CI 0 CH ₃ CH ₂ CH = CH ₂ (Table 7)

(Table 8)

Compound Ym GR ¹ Melting point number (° C)

1-203 3-CI 0 CH ₃ CH ₂ 0CH ₃

1-204 4-CI 0 CH ₃ CH ₂ 0CH ₃

1-205 3-CF ₃ 0 CH ₃ CH ₂ 0CH ₃

1-206 4-CF3 0 CH ₃ CH ₂ 0CH ₃

1-207 3, 4- (CH3) 2 0 CH ₃ CH2 OCH3

1-208 3.4-Cl ₂ 0 CH ₃ CH2 OCH3

1-209 H 0 CH ₃ CH ₂ 0C ₂ H ₅

1-210 3- CI 0 CH ₃ CH ₂ 0C ₂ H ₅

1 211 4- CI 0 CH ₃ CH ₂ 0C ₂ H ₅

1-212 3-CH3 0 CH ₃ CH ₂ 0C ₂ H ₅

1-213 4-CH3 0 CH ₃ CH ₂ 0C ₂ H ₅

1-214 H 0 CH ₃ CH ₂ SCH ₃

1-215 2-CH3 0 CH ₃ CH2SCH3

1-216 3-CH3 0 CH ₃ CH ₂ SCH ₃

1-217 4-CH3 0 CH ₃ CH2SCH3

1-218 2-OCH3 0 CH ₃ CH2SCH3

1-219 3-OCH3 0 CH ₃ CH2SCH3

1-220 4-OCH3 0 CH ₃ CH2SCH3

1-221 2-F 0 CH ₃ CH2SCH3

1-222 3-F 0 CH ₃ CH2SCH3

1-223 4-F 0 CH ₃ CH ₂ SCH ₃

1-224 2- CI 0 CH ₃ CH ₂ SCH ₃

1-225 3-C1 0 CH3 CH2SCH3

1-226 4-CI 0 CH ₃ CH ₂ SCH ₃

1-227 3-CF3 0 CH ₃ CH ₂ SCH ₃

1-228 4-CF3 0 CH ₃ CH ₂ SCH ₃

1-229 3, 4- (CH ₃ ) ₂₀ CH ₃ CH ₂ SCH ₃

1-230 3, 4-Cl ₂ 0 CH ₃ CH ₂ SCH ₃

1-231 H 0 CH ₃ COCH3 oil

1-232 H 0 CH ₃ C0C ₂ H ₅

1-233 H 0 CH ₃ C0C ₄ Hg

1-234 H 0 CH ₃ co-Q (Table 9)

Compound Ym G R Melting point number "^ (° C)

1-235 3-CH ₃ 0 CH ₃ COCH3

1-236 4-CH3 0 CH ₃ COCH3

1-237 2-C1 0 CH ₃ COCH3

1-238 3-C1 0 CH ₃ C0CH ₃

1-239 4-C1 0 CH ₃ COCH3

1-240 3-CF ₃ 0 CH ₃ COCH3

1-241 4-CF ₃ 0 CH ₃ COCH3

1-242 3, 4- (CH ₃ ) ₂ 0 CH ₃ COCH3

1-243 H 0 CH ₃ COOCH3

1-244 H 0 CH ₃ COOC2H5

1-245 H s CH ₃ H 85-88

1-246 3-CH3 s CH ₃ H

1-247 4-CH3 s CH ₃ H 105-107

1-248 2- CI s CH ₃ H

1-249 3- CI s CH ₃ H

1-250 4- CI s CH ₃ H

1-251 3-CF3 s CH ₃ H

1-252 4-CF ₃ s CH ₃ H

1-253 H NH CH ₃ H 115-118

1-254 3-H3 Orchid CH ₃ H 148-151

1-255 4-CH3 NH CH ₃ H

1-256 3-CI NH CH ₃ H

1-257 4-CI NH CH ₃ H

1-258 3-CF3 NH CH ₃ H

1-259 4-CF ₃ NH CH ₃ H

1-260 H NH C ₂ H ₅ H 136-137

1-261 H NH C3H7 H

1-262 H NCH3 CH ₃ H oil

1-263 H NC ₂ H ₅ C ₂ H ₅ H

1-264 H 0 CH ₃ OCH3 oil

1-265 2-H3 0 OCH3

1-266 3-CH3 0 CH ₃ OCH3 oil (Table 10

/

Compound Ym G R R Melting point

(° C)

1-267 4-CH ₃ 0 CH ₃ 0CH ₃

1-268 2-OCH3 0 CH ₃ OCH3

1-269 3-OCH3 0 CH ₃ OCH3

1-270 4-OCH3 0 CH ₃ OCH3

1-271 2-F 0 CH ₃ OCH3

1-272 3-F 0 CH ₃ OCH3

1-273 4-F 0 CH ₃ OCH3

1-274 2-CI 0 CH ₃ OCH3

1-275 3-CI 0 CH ₃ OCH3 Oily substance

1-276 4-CI 0 CH ₃ OCH3

1-277 3-CF3 0 CH ₃ OCH3 oil

1-278 4-F3 0 CH ₃ OCH3

1-279 3 4- (CH ₃ ) 20 CH ₃ OCH3

One on

3, 4-CI2 u CH ₃ O H3

H CH ₃ OC2 H5 1 8 2- CH ₃ 0 CH ₃ 0 C2

3- H3 0 CH ₃ 0C ₂ H ₅

1-284 4-CH3 0 CH ₃ OC2H5

_{1-285 2-OCH3 0 CH 3 0C} 2 H 5

1-286 3-OCH3 0 CH ₃ 0C ₂ H ₅

1-287 4-OCH3 0 CH3 0C ₂

1-288 2-F 0 CH ₃ 0C ₂ H ₅

1-289 3-F 0 CH ₃ 0C ₂ H ₅

1-290 4-F 0 CH ₃ 0C ₂ H ₅

1-291 2-CI 0 CH ₃ 0C ₂ H ₅

1-292 3-CI 0 CH ₃ 0C ₂ H ₅

1-293 4-C1 0 CH ₃ 0C ₂ H ₅

1-294 3-CF3 0 CH ₃ 0C ₂ H ₅

1-295 4-CF3 0 CH ₃ 0C ₂ H ₅

1-296 3, 4- (CH ₃ ) ₂ 0 CH ₃ 0C ₂ H ₅

1-297 3, 4-Cl ₂ 0 CH ₃ 0C ₂ H ₅

1-298 4-0 0 CH ₃ H 134-136 (Table 11)

Compound Ym X ¹ X ² χ3 X ⁴ Melting point number (.c)

2-1 H CH ₃ HHH 91-94

2-2 3-FH ₃ HHH

2-3 4-F CH ₃ HHH

2-4 3-C1 CH ₃ HHH

2-5 4-C1 CH ₃ HHH

2-6 3-CH ₃ CH ₃ HHH

2-7 4-CH3 CH ₃ HHH

2-8 3- ₂ H ₅ CH ₃ HHH

2-9 4-C ₂ ¾ CH ₃ HHH

2-10 3-OCH3 CH ₃ HHH

2-11 4-OCH3 CH ₃ HHH

^{_{2-12 3, 4 - (CH 3}} ) 2 CH 3 HHH

2-13 3, 5- (CH ₃ ) ₂ CH ₃ HHH

2-14 2, 4-Cl ₂ H ₃ HHH

2-15 3, 4-Cl ₂ CH ₃ HHH

2-16 3, 5-Cl ₂ CH ₃ HHH

2-17 H H F H H 66-69

2-18 3-F H F H H H

2-19 4-F H F H H

2-20 3-C1 H F H H

2-21 4- CI H F H H 87-90

2-22 3-CH3 H F H H Oily substance

2-23 -CH3 H F H H

2-24 3-C ₂ H ₅ HFHH

2-25 4-C ₂ H ₅ HFHH

2-26 3-OCH3 H F H H

2-27 4-OCH3 H F H H

2-28 3-CF3 HFHH (Table 12)

Compound Ym. \ 2 X3 X4 Melting point number (T)

2-29 4-CF ₃ HFHH

2-30 2, 4-Cl ₂ HFHH

2-31 3, 4-Cl ₂ HFHH

2-32 3, 4- (CH ₃ ) ₂ HFHH

2-33 3, 5- (CH ₃ ) ₂ HFHH

2-34 H H CI H H

2-35 3-F H CI H H

2-36 4-F H CI H H

2-37 3-CI H CI H H

2-38 4-CI H CI H H

2-39 3- H3 H CI H H

2-40 -CH3 H CI H H

2-41 3-C ₂ H ₅ H CI HH

2-42 -C ₂ H ₅ H CI HH

2-43 3-OCH3 H CI H H

2-44 4-OCH3 H CI H H,

2-45 3-CF3 H CI H H

2-46 4-CF3 H CI H H

2-47 3,4- Cl ₂ H CI HH

2-48 3.4- (CH ₃ ) ₂ H CI HH

2-49 3, 5- (CH ₃ ) ₂ H CI HH

2-50 HH CH ₃ HH 67-70

2-51 3-FH CH ₃ HH

2-52 4-FH CH ₃ HH

2-53 3-C1 H CH ₃ HH

2-54 4-C1 H CH ₃ HH 111-114

2-55 3-CH3 H CH ₃ HH

2-56 4-CH3 HH ₃ HH 91-94

2-57 3-C ₂ H ₅ H CH ₃ HH

2-58 4-C ₂ H ₅ H CH ₃ HH

2-59 4-OCH3 H CH ₃ HH (Table 13)

Compound Ym X ¹ X2 X Melting point

■ .mouth

(.C)

2-60 3-CF ₃ H CH ₃ HH

2-61 4-CF3 H CH ₃ HH

2-62 3,4- Cl ₂ H CH ₃ HH

2-63 3.4- (CH ₃ ) ₂ HH ₃ HH

2-64 3, 5- (CH ₃ ) ₂ H CH ₃ HH

2-65 H H OCH3 H H 70-73

2-66 3-F H OCH3 H H

2-67 4-F H OCH3 H H

2-68 3-CI H OCH3 H H

2-69 4- CI H OCH3 H H

2-70 3-CH3 H OCH3 H H

2-71 4-CH3 H OCH3 H H 73-76

2-72 3-C ₂ H ₅ H OCH3 HH

2-73 -C ₂ H ₅ H OCH3 HH

2-74 4-OCH3 H OCH3 H H

2-75 3-CF3 H OCH3 H H

2-76 4- F3 H OCH3 H H

2-77 3.4-Cl ₂ H OCH3 HH

2-78 3.4- (CH ₃ ) ₂ H OCH3 HH

2-79 3, 5- (CH ₃ ) ₂ H OCH3 HH

2-80 H H H CI H

2-81 3-F H H CI H

2-82 4-F H H CI H

2-83 3-CI H H CI H

2-84 4- CI H H CI H

2-85 3-CH3 H H CI H

2-86 4-CH3 H H CI H

2-87 3-CF3 H H CI H

2-88 4-CF3 H H CI H

2-89 3, 4-Cl ₂ HH CI H

2-90 3, 4- (CH ₃ ) ₂ HH CI H (Table 14)

(Table 15)

(Table 16)

Compound Ym X ¹ X2, X'3 Melting point number (° C)

2-153 4-CH = CH ₂ HHHF

2-154 3- N H H H F

2-155 4-NH ₂ HHHF

2-156 3-HCH3 H H H F

2-157 4-HCH3 H H H F

2-158 3-N ^; (CH ₃ ) ₂ HHHF

2-159 4 \ '(CH ₃ ) ₂ HHHF

2-160 3-NHCOCH3 H H H F

2-161 4-.NHCOCH3 H H H F

2-162 3-HCOC2H5 H H H F

2-163 4- HC0C ₂ H ₅ HHHF

2-164 3.4-Cl ₂ HHHF 97-98

2-165 H H H F

2-166 3.4- (CH ₃ ) ₂ HHHF oily substance

2-167 3, 5- (CH ₃ ) ₂ HHHF

2-168 3-F, 4-CH3 H H H F

2-169 3 CI, 4-CH3 H H H F

2-170 3-CI, 4-CF3 H H H F

2-171 4-F, 3-CH3 H H H F 64-66

2-172 4-Cl, 3-CH3 H H H F

2-173 4-Br, 3-CH3 H H H F

2-174 4-Cl, 3-OCH3 H H H F

2-175 4-Cl, 3-OC2H5 H H H F

_{2-176 3, 5- (CH 3)} 2 .4-FHHHF

_{2-177 3- 0 2, 4-CH3} HHHF

2-178 3, 5- (CF ₃ ) ₂ HHHF

2-179 2, 4- (CF ₃ ) ₂ HHHF

2-180 5-Br, 2-OCH3 H H H F

2-181 2, 4, 6- (CH ₃ ) 3 HHHF

2-182 H H H H CI 88-91

2-183 3-FHHH CI 81-82 (Table 17)

(Table 18)

Compound Ym χΐ X ² X3 Melting point

(° C)

2-215 3-SCF ₃ HHH CI 124-126

2-216 4-SCF3 H H H CI

2-217 3-COOCH3 H H H CI

2-218 4-COOCH3 H H H CI

2-219 3- C00C ₂ ¾ HHH CI

2-220 4-C00C ₂ H ₅ HHH CI 119-122

2-221 3- 圆₂ HHH CI

2-222 4-圆 2 H H H CI

2-223 3-N0 ₂ HHH CI 198-201

2-224 4- 0 ₂ HHH CI

2-225 3-CN H H H CI

2-226 4-C H H H CI 161 -164

2-227 3-SCH3 H H H CI

2-228 4-SCH3 H H H CI

2-229 3-SOCH3 H H H CI

2-230 4-SOCH3 H H H CI

2-231 3-S0 ₂ CH ₃ HHH CI

2-232 4-S0 ₂ CH ₃ HHH CI

2-233 4-CH = CH ₂ HHH CI

2-234 3-thigh 2 H H H CI

2-235 4-NH ₂ HHH CI

2-236 3-NHCH3 H H H CI

2-237 4-NHCH3 H H H CI

2-238 3- (CH ₃ ) ₂ HHH CI

2-239 4-N (CH ₃ ) ₂ HHH CI

2-240 3-NHCOCH3 H H H CI

2-241 4-NHCOCH3 H H H CI

2-242 3-NHC0C ₂ H ₅ HHH CI

2-243 4-NHCOC2H H H H CI

2-244 3, 4-Cl ₂ HHH CI

2-245 3, 5-Cl ₂ HHH CI 114-117 (Table 19

Compound Ym X ¹ X2 X3 Melting point number CO

2-246 3, 4- (CH ₃ ) ₂ HHH CI 67-68

2-247 3, 5- (CH ₃ ) ₂ HHH CI 91-94

2-248 3-F, 4-CH ₃ HHH CI 97-98

2-249 3- CI, 4-CH3 H H H CI 84-85

2-250 3-CI, 4-CF3 H H H CI

2-251 4-F, 3-CH3 H H H CI 75-78

2-252 4- CI, 3-CH3 H H H CI

2-253 4-Br, 3-CH3 H H H CI

2-254 4- CI, 3-OCH3 H H H CI

2-255 4- CI, 3-0C ₂ H ₅ HHH CI

2-256 3, 5- (CH ₃ ) ₂ , 4-FHHH CI

2-257 3-NO2, 4-CH3 H H H CI 119-122

2-258 3, 5- (CF ₃ ) ₂ HHH CI 170-171

2-259 2, 4- (CF ₃ ) ₂ HHH CI

2-260 5-Br, 2-OCH3 H H H CI

2-261 2, 4, 6- (CH ₃ ) ₃ HHH CI 160-161

2-262 H H H H Br

2-263 3-F H H H Br

2-264 4-F H H H Br

2-265 3- CI II H H Br

2-266 4-C1 H H H Br 133-136

2-267 3-CH3 H H H Br

2-268 -CH3 H H H Br 114-117

2-269 3-C ₂ H ₅ HHH Br

2-270 4-C ₂ H ₅ HHH Br

2-271 3-C3H7- 1 H H H Br

2-272 4-C3H7- 1 H H H Br

2-273 3-C ₄ Hq-t HHH Br

2-274 4-C ₄ Hg-t HHH Br

2-275 3-OCH3 H H H Br

2-276 4-OCH3 HHH Br (Table 20)

r Table 2 l)

Compound Ym X ¹ X2 X3 X4 Melting point

(.C)

2-308 4-FHHH CF ₃

2-309 3- CI HHH CF ₃

2-310 4- CI HHH CF ₃

2-311 3-CH ₃ HHH CF ₃

2-312 4-CH3 HHH CF ₃

2-313 3-C ₂ H ₅ HHH CF ₃

2-314 4-C2H5 HHH CF ₃

2-315 3-C3H7- 1 HHH CF ₃

2-316 4- C ₃ H ₇ -i HHH CF ₃

2-317 3-C ₄ Hg-t HHH CF ₃

2-318 4-C ₄ Hg-t HHH CF ₃

2-319 3-OCH3 HHH CF ₃

2-320 4-OCH3 HHH CF ₃

2-321 3-CF3 HHH CF ₃

2-322 4-F3 HHH CF ₃

2-323 3, 4-Cl ₂ HHH CF ₃

2-324 3, 4- (CH ₃ ) ₂ HHH CF ₃

2-325 3, 5- (CH ₃ ) ₂ HHH CF ₃

2-326 3-OCF3 HHH CF ₃

2-327 4-OCF3 HHH CF ₃

2-328 H H H H OCH3 77-79

2-329 3-F H H H OCH3

2-330 4-F H H H OCH3

2-331 3- CI H H H OCH3 89-92

2-332 4-CI H H H OCH3 116-119

2-333 3-CH3 H H H OCH3 Oily substance

2-334 4-CH3 H H H OCH3 107-108

2-335 3-C ₂ H ₅ HHH OCH3

2-336 4-C ₂ H ₅ HHH OCH3

2-337 3-C3H7- 1 H H H OCH3

2-338 4-C3H7- 1 HHH OCH3 (Table 22)

Compound Ym X ¹ X ² X3 Melting point

(.C)

2-339 3-C ₄ Hg-t HHHO H3

2-340 4-C ₄ Hg-t HHH OCH3

2-341 3-OCH3 H H H OCH3

2-342 4-OCH3 H H H OCH3

2-343 3-CF3 H H H OCH3 78-81

2-344 4-CF3 H H H OCH3 110-113

2-345 3, 4-Cl ₂ HHH OCH3

2-346 3, 4- (CH ₃ ) ₂ HHHO H3 Oil

2-347 3, 5- (CH ₃ ) ₂ HHH OCH3

2-348 3-OCF3 H H H OCH3

2-349 4-OCF3 H H H OCH3

2-350 HHHH 0CHF ₂

2-351 3-FHHH 0CHF ₂

2-352 4-FHHH 0CHF ₂

2-353 3-CI HHH 0CHF ₂

2-354 4-CI HHH 0CHF ₂

2-355 3-CH3 HHH 0CHF ₂

2-356 4-CH ₃ HHH 0CHF ₂

2-357 3-C ₂ H ₅ HHH 0CHF ₂

2-358 4-C ₂ H ₅ HHH 0CHF ₂

2-359 3-C3H7 HHH 0CHF ₂

2-360 4-C3H7 HHH 0CHF ₂

2-361 3-C ₄ Hg-t HHH 0CHF ₂

2-362 4- C4H9-t HHH 0CHF ₂

2-363 3-OCH3 HHH 0CHF ₂

2-364 4-OCH3 HHH 0CHF ₂

2-365 3-CF3 HHH 0CHF ₂

2-366 4-F3 HHH 0CHF ₂

2-367 3, 4-Cl ₂ HHH 0CHF ₂

2-368 3, 4- (CH ₃ ) ₂ HHH 0CHF ₂

2-369 3, ^5- (CH ₃ ) ₂ HHH 0CHF ₂ (Table 23)

(Table 24 :)

Compound Ym X ² X3 X ⁴ Melting point number (° C)

2-401 3-COCH3 H H H F

2-402 4-COCH3 H-H H F

2-403 3-Br H H H F

2-404 4-Br H H H F

2-405 3, 4-(OH) 2 H H H F

2-406 3, 4- (OCH3) 2 H H H F

2-407 3, 4- (0CH ₂ 0) HHHF

2-408 H H H F

2-409 2, 4-Cl ₂ HHHF

2-410 2, 5-Cl ₂ HHHF

2-411 2, 4-F ₂ HHHF

2-412 3, 4-F ₂ HHHF 55-56

2-413 2, 5-F? H H H F

2-414 2-F, 4- CI H H H F

2-415 3-F, 4-CI H H H F

2-416 3-CI, 4-F H H H F 101-103

2-417 2, 4- (CH ₃ ) ₂ HHHF

2-418 2, 5- (CH ₃ ) ₂ HHHF

2-419 2-F, 4-CH3 H H H F

2-420 2-CI, 4-CH3 H H H F

2-421 2-F, 5-CH3 H H H F

2-422 2- CI, 5-CH3 H H H F

2-423 2-OCH3, 5-CH3 H H H F

2-424 3-C ₂ H ₅ , 4-CI HHHF

2-425 3-CN, 4-F H H H F

2-426 3-CN, 4- CI H H H F

2-427 3-CN, 4-OCH3 H H H F

2-428 3-COCH3, 4-OCH3 H H H F

2-429 3, 5-(CH ₃ ) ₂ , 4-CI HHHF

2-430 3, 5- (CH ₃ ) ₂ , 4-OCH3 HHHF

2-431 3, 4, 5- (CH ₃ ) ₃ HHHF (Table 25)

Compound Ym X ² X3 X ⁴ Melting point

(.C)

2-432 3, 4, 5- (0CH ₃ ) ₃ HHHF

2-433 3, 5- (C ₂ H ₅ ) ₂ , 4-Cl HHHF

2-434 3-CF ₃ , 4-FHHHF

2-435 3-CF3, 4-CI H H H F

2-436 H H H F

2-437 2-F, 5-CF3 H H H F

2-438 2- CI, 5-CF3 H H H F

2-439 2-F, 3-CF3 H H H F

2-440 2-F, 4-CF3 H H H F

2-441 3, 4-F ₂ , 5-CF3 HHHF

2-442 3-COOCH3, 4-CI H H H F

2-443 3-COOCH3, 4-CH3 H H H F

2-444 3- C≡CH H H H F

2-445 4-C≡CH H H H F

2-446 H H H F

2-447 4-C≡C-CH ₃ HHHF

2-448 3-OH H H H CI Oil

2-449 4- OH H H H CI 168-171

2-450 3-COCH3 H H H CI 84-86

2-451 4-COCH3 H H H CI 122-125

2-452 3- Br H H H CI

2-453 4-Br H H H CI 124-127

2-454 3, 4- (OH) 2 H H H CI 193-196

2-455 3, 4- (0CH ₃ ) ₂ HHH CI 113-116

2-456 3, 4- (0CH ₂ 0) HHH CI 106-107

2-457 2, 3-Cl ₂ HHH CI 159-162

2-458 2.4-Cl ₂ HHH CI oil

2-459 2, 5-Cl ₂ HHH CI

2-460 2, 4-F ₂ HHH CI

2-461 3, 4-F ₂ HHH CI 68-71

2-462 2, 5-F2 HHH CI (Table 26

(Table 27)

('Table 28)

(Table 29)

Compound Ym. \ 2 XX ⁴ melting point

■ ψ ,. Χ = 3_

CO

2-556 3-CF ₃ HHHI

2-557 -CF3 H H H I

2-558 3-COCH3 H H H I

2-559 4-COCH3 H H H I

2-560 2, 4- (CH ₃ ) 2 HHHI

2-561 2, 5- (CH ₃ ) ₂ HHHI

2-562 3, 4- (CH ₃ ) ₂ HHHI

2-563 3, 5- (CH ₃ ) ₂ HHHI

2-564 3, 4- (OCH3) 2 H H H I

2-565 2, 4-Cl ₂ HHHI

2-566 2, 5-Cl ₂ HHHI

2-567 3, 4-Cl ₂ HHHI

2-568 2, 4-F ₂ HHHI

2-569 2, 5-F ₂ HHHI

2-570 3, 4-F ₂ HHHI

2-571 2-F, 4-CI H H H I

2-572 3-F, 4- CI H H H I

2-573 3-C1. 4-F H H H I

2-574 2, 4- (CH ₃ ) ₂ HHHI

2-575 2, 5- (CH ₃ ) ₂ HHHI

2-576 2-F, 4-CH3 H H H I

2-577 2-CI, 4-CH3 H H H I

2-578 2-F, 5-CH3 H H H I

2-579 2-CI, 5-CH3 H H H I

2-580 2-OCH3, 5-CH3 H H H I

2-581 3-CF3, 4-F H H H I

2-582 3-CF3, 4- CI H H H I

2-583 3-F, 5-CF3 H H H I

2-584 2-F, 5-CF3 H H H I

2-585 2- CI, 5-CF3 H H H I

2-586 2-F, 3-CF3 HHHI (Table 30)

Compound Ym X2. \ 3 Melting point number (.c)

2-587 2-F, 4-CF ₃ HHHI

2-588 3-COCH3 HHH CH ₃

2-589 4-COCH3 HHH CH ₃

2-590 3-Br HHH CH ₃

2-591 4-Br HHH CH ₃

2-592 3, 4- (OH) 2 HHH CH ₃

2-593 3, 4-(0CH ₃ ) 2 HHH CH ₃

2-594 3, 4-(0CH ₂ 0) HHH CH ₃

2-595 2, 4-Cl ₂ HHH CH ₃

2-596 2, 5-Cl ₂ HHH CH ₃

2-597 2, 4-F ₂ HHH CH ₃

2-598 3.4-F ₂ HHH CH ₃

2-599 2, 5-F ₂ HHH CH ₃

2-600 2-F, 4- CI HHH CH ₃

2-601 3-F, 4-CI HHH CH ₃

2-602 3-CI, 4-FHHH CH ₃

2-603 2, 4- (CH ₃ ) ₂ HHH CH ₃

2-604 2, 5-(CH ₃ ) ₂ HHH CH ₃

2-605 2-F, 4-CH3 HHH CH ₃

2-606 2- CI, 4-CH3 HHH CH ₃

2-607 2-F, 5-CH3 HHH CH ₃

2-608 2-Cl, 5-CH3 HHH CH ₃

2-609 2-0CH _3> 5-CH3 HHH C¾

2-610 3-C H5, 4-Cl H H H CH3

2-611 3-CN, 4-FHHH CH ₃

2-612 3-CN, 4-Cl HHH CH ₃

2-613 3-CN, 4-OCH3 HHH CH ₃

2-614 3-COCH3, 4-OCH3 HHH CH ₃

2-615 3, 5- (CH ₃ ) ₂ , 4-Cl HHH CH ₃

2-616 3, 5- (CH ₃ ) 2, 4-OCH3 HHH CH ₃

2-617 3, 4, 5- (CH ₃ ) 3 HHH. CH ₃ (Table 3 1

Compound Ym χΐ X2. \ 3 Melting point number (° C)

III

2-618 3, 4, 5-(0CH ₃ ) ₃ HHH CH ₃

2-619 3, 5- (C ₂ H ₅ ) ₂ , 4-CI HHH CH ₃

2-620 3-CF _3. .4-FHHHH ₃

2-621 3-CF3, 4-CI HHHH ₃

2-622 3-F, 5-CF3 HHH CH ₃

2-623 2-F, 5-CF3 HHH CH ₃

2-624 2- CI, 5-CF3 HHH CH ₃

2-625 2-F, 3-CF3 HHH CH ₃

2-626 2-F, 4-CF3 HHH CH ₃

2-627 3, 4-F ₂ , 5-CF3 HHHH ₃

2-628 3-COOCH3, 4- CI HHH CH ₃

2-629 3-COOCH3, 4-CH3 HHH CH ₃

2-630 3-C≡CH HHH CH ₃

2-631 4-C≡CH HHH CH ₃

2-632 HHH CH ₃

2-633 4-C≡C-CH ₃ HHH CH ₃

• 2-634 HHH CH ₃ OCH3

2-635 3-FHH CH ₃ OCH3

2-636 4-FHH CH ₃ OCH3

2-637 3-CI HH CH ₃ OCH3

2-638 4-C1 HH CH ₃ OCH3

2-639 3-Br HH CH ₃ OCH3

2-640 4-Br HH CH ₃ OCH3

2-641 3-CH3 HH CH ₃ OCH3

2-642 4-CH3 HH CH ₃ OCH3

2-643 3-C ₂ H ₅ HH CH ₃ OCH3

2-644 4-C ₂ H ₅ HH CH ₃ OCH3

2-645 3-OCH3 HH CH ₃ OCH3

2-646 4-OCH3 HH CH ₃ OCH3

2-647 3-CF3 HH CH ₃ OCH3

2-648 -CF3 HH CH ₃ OCH3 (Table 32)

Compound Ym χΐ X2 X3 X4 Melting point number (° C)

_{2-649 3-COCH3 HH CH 3 0CH} 3

2-650 4-COCH3 HH CH ₃ OCH3

2-651 2, 4- (CH ₃ ) 2 HH CH ₃ OCH3

2-652 2, 5- (CH ₃ ) 2 HH CH ₃ OCH3

2-653 3, 4- (CH ₃ ) 2 HH CH ₃ OCH3

2-654 3, 5- (CH ₃ ) 2 HH CH ₃ OCH3

2-655 3, 4- (OCH3) 9 HH CH ₃ OCH3

2-656 2- 4-Cl ₂ HH CH ₃ OCH3

2-657 2,5-Cl ₂ HH CH ₃ O H3

2-658 3, 4-Cl ₂ HH CH ₃ OCH3

2-659 2, 4-F ₂ HH CH ₃ OCH3

2-660 2, 5-F ₂ HHH ₃ OCH3

2-661 3, 4-F ₂ HH CH ₃ OCH3

2-662 2-F, 4-CI HH CH ₃ OCH3

2-663 3-F, 4-CI HH CH ₃ OCH3

2-664 3- CI, 4-FHH CH ₃ OCH3

2-665 2, 4- (CH ₃ ) ₂ HH CH ₃ OCH3

2-666 2, 5- (CH ₃ ) ₂ HH CH ₃ OCH3

2-667 2-F, 4-CH3 HH CH ₃ OCH3

2-668 2-CI, 4-CH3 HH CH ₃ OCH3

2-669 2-F, 5-CH3 HH CH ₃ OCH3

2-670 2-Ci, 5-CH3 HH CH ₃ OCH3

2-671 2-OCH3, 5-CH3 HH CH ₃ OCH3

2-672 3-CF3, 4-FHH CH ₃ OCH3

2-673 3-CF3, 4- CI HH CH ₃ OCH3

2-674 3-F, 5-CF3 HH CH ₃ OCH3

2-675 2-F, 5-CF3 HH CH ₃ OCH3

2-676 2-Cl, 5-CF3 HH CH ₃ OCH3

2-677 2-F, 3-CF3 HH CH ₃ OCH3

2-678 2-F, 4-CF3 HH CH ₃ OCH3

2-679 HHH CI OCH3 (Table 33)

Compound Ym, \ 2 X3 melting point

(.C)

2-680 3-F H H CI 0CH3

2-681 4-F H H CI 0CH3

2-682 3- CI H H CI 0CH3

2-683 4- CI H H CI 0CH3

2-684 3- Br H H CI 0CH3

2-685 4- Br H H CI 0CH3

2-686 3-CH ₃ HH CI 0CH3

2-687 4-CH3 H H CI 0CH3

2-688 3-C ₂ H ₅ HH CI 0CH3

2-689 4-C ₂ H ₅ HH CI 0CH3

2-690 3-OCH3 H H CI 0CH3

2-691 4-OCH3 H H CI 0CH3

2-692 3-CF3 H H CI 0CH3

2-693 4-CF3 H H CI 0CH3

2-694 3-COCH3 H H CI 0CH3

2-695 4-COCH3 H H CI 0CH3

2-696 2, 4- (CH ₃ ) ₂ HH CI 0CH3

2-697 2.5- (CH ₃ ) ₂ HH CI 0CH3

2-698 3, 4- (CH ₃ ) ₂ HH CI 0CH3

2-699 3.5- (CH ₃ ) ₂ HH CI 0CH3

2-700 3, 4- (0CH ₃ ) ₂ HH CI 0CH3

2-701 2.4-Cl ₂ HH CI 0CH3

2-702 2, 5-Cl ₂ HH CI 0CH3

2-703 3.-C12 H H CI 0CH3

2-704 2.4-F ₂ HH CI OCH3

2-705 2, 5-F ₂ HH CI 0CH3

2-706 3, 4-F ₂ HH CI 0CH3

2-707 2-F, 4- CI H H CI 0CH3

2-708 3-F, 4- CI H H CI 0CH3

2-709 3-Cl, 4-F H H CI 0CH3

2-710 2, 4- (CH ₃ ) ₂ HH CI 0CH3 (Table 34)

Compound Υπι X2 X3 Melting point number (° C)

2-711 2, 5- (CH ₃ ) ₂ HH CI 0CH ₃

2-712 2-F, 4-CHq H H CI 0CH3

2-713 2-Cl, 4-CH ₃ HH CI 0CH3

2-714 2-F, 0-CH3 H H CI 0CH3

2-715 2-Cl, 5-CH3 H H CI 0CH3

2-716 H H Π

2-717 3-CF3, 4-FHH CI 0CH ₃

2-718 3-CF3, 4- CI H H CI OCH3

2-719 3-F, 5-CF3 H H CI OCH3

2-720 2-F, 5-CF3 H H CI OCH3

2-721 2-Cl, 5-CF3 H H CI OCH3

2-722 2-F, 3-CF3 H H CI OCH3

2-723 2-F, 4-CF3 HH CI OCH3

(Table 3 5

,, 9

Compound Ym X 丄 X3 A Melting point number "^ c)

3-1 HHHHH CH (CH ₃ ) oily substance

3-2 3-FHHHH CH (CH ₃ )

3-3 4-FHHHH CH (CH ₃ )

3-4 3-Cl HHHH CH (CH ₃ )

3-5 4- CI HHHH CH (CH ₃ ) 105-107

3-6 -CH ₃ HHHH CH (CH ₃ ) oily substance

3-7 4-CH3 HHHH CH (CH ₃ ) 99-101

3-8 3-C ₂ H ₅ HHHH CH (CH ₃ )

3-9 4-C ₂ H ₅ HHHH CH (CH ₃ )

3-10 3-C3H7-1 HHHH CH (CH ₃ )

3-11 4-C3H7-1 HHHH CH (CH ₃ )

3-12 3-C ₄ Hg-t HHHH CH (CH ₃ )

3-13 4-C ₄ Hg-t HHHH CH (CH ₃ )

3-14 3-OCH3 HHHH CH (CH 3)

3-15 4-OCH3 HHHH CH (CH 3) 117-119

3-16 3-CF3 HHHH CH (CH ₃ ) Oil

3-17 4-CF3 HHHH CH (CH ₃ ) 87-89

3-18 2.4-Cl ₂ HHHH CH (CH ₃ ) Oil

3-19 3, 4-Cl ₂ HHHH CH (CH ₃ )

3-20 3, 5-Cl ₂ HHHH CH (CH ₃ ) Oil

3-21 3-Cl, 4-FHHHH CH (CH ₃ ) 55-58

3-22 3, 4- (CH ₃ ) ₂ HHHH CH (CH ₃ )

3-23 3,5- (CH ₃ ) ₂ HHHH CH (CH ₃ )

3-24 3-OCF3 HHHH CH (CH ₃ )

3-25 4-OCF3 HHHH CH (CH ₃ )

3-26 HHHHF CH (CH ₃ ) oil

3-27 3-FHHHF CH (CH ₃ )

3-28 4-FHHHF CH (CH ₃ ) 104-105 3 6)

Compound Ym X ¹ X ² X3 X ⁴ A Melting point

(hand)

3-29 3-CI HHHF CH (CH ₃ )

3-30 4-C1 HHHF CH (CH ₃ ) 131-134

3-31 3-CH ₃ HHHF CH (CH ₃ )

3-32 4-CH3 HHHF CH (CH ₃ ) 106-107

3-33 3- C ₂ H ₅ HHHF CH (CH ₃ )

3-34 4-¾Η ₅ HHHF CH (CH ₃ )

3-35 3- 3H7-1 HHHF CH (CH ₃ )

3-36 4-C3H7-1 HHHF CH (CH ₃ )

3-37 3-C ₄ Hg-t HHHF CH (CH ₃ )

3-38 4-C ₄ Hg-t HHHF CH (CH ₃ )

3-39 3-OCH3 HHHF CH (CH ₃ )

3-40 4-OCH3 HHHF CH (CH ₃ )

3-41 3-CF3 HHHF CH (CH ₃ ) 126-128

3-42 4-CF3 HHHF CH (CH ₃ ) 97-100

3-43 2, 4-Cl ₂ HHHF CH (CH ₃ )

3-44 3, 4-Cl ₂ HHHF CH (CH ₃ )

3-45 3, 5-Cl ₂ HHHF CH (CH ₃ )

3-46 3- CI, 4-FHHHF CH (CH ₃ )

3-47 3, 4- (CH ₃ ) ₂ HHHF CH (CH ₃ )

3-48 3, 5- (CH ₃ ) ₂ HHHF CH (CH ₃ )

3-49 3-OCF3 HHHF CH (CH ₃ )

-50 4-OCF3 HHHF CH (CH ₃ )

3-51 HHHH CI CH (CH ₃ ) 130-133

3-52 3-FHHH CI CH (CH ₃ )

-53 4-FHHH CI CH (CH ₃ )

-54 3-C1 HHH CI CH (CH ₃ )

-55 4- CI HHH CI CH (CH ₃ ) 135-138 -56 3- H3 HHH CI CH (CH ₃ )

-57 4-CH3 HHH CI CH (CH ₃ ) 114-117-58 3-C ₂ H ₅ HHH CI CH (CH ₃ )

-59 4-C ₂ H ₅ HHH CI CH (CH ₃ ) (Table 37)

Compound Ym X ¹ X ² X3 X ⁴ A Melting point

(.C)

3-60 3-C ₃ H ₇ -i HHH CI CH (CH ₃ )

3-61 4-C3H7-1 HHH CI CH (CH ₃ )

3-62 3-C ₄ Hg-t HHH CI CH (CH ₃ )

3-63 4-C4H9- t HHH CI CH (CH ₃ )

3-64 3-OCH3 HHH CI CH (CH ₃ )

3-65 4-OCH3 HHH CI CH (CH ₃ )

3-66 3-CF3 HHH CI CH (CH ₃ ) 143-146

3-67 4-CF3 HHH CI CH (CH ₃ )

3 68 2, 4-Cl ₂ HHH CI CH (CH ₃ )

3-69 3, 4-Cl ₂ HHH CI CH (CH ₃ )

3-70 3, 5-Cl ₂ HHH CI CH (CH ₃ )

3-71 3-CI, 4-FHHH CI CH (CH ₃ )

3-72 3, 4- (CH ₃ ) ₂ HHH CI CH (CH ₃ )

3-73 3, 5- (CH ₃ ) ₂ HHH CI CH (CH ₃ )

3-74 3-OCF3 HHH CI CH (CH ₃ )

3-75 4-OCF3 HHH CI CH (CH ₃ )

_{3-76 HHHH 0CH3 CH (CH 3)} 130-131

3-77 3-FHHH 0CH3 CH (CH ₃ )

3-78 4-FHHH 0CH3 CH (CH ₃ )

3-79 3-CI HHH 0CH3 CH (CH ₃ )

3-80 4-CI HHH 0CH3 CH (CH ₃ ) 140-143

3-81 3- H3 HHH 0CH3 CH (CH ₃ )

3-82 4-CH3 HHH 0CH3 CH (CH ₃ )

3-83 3-C ₂ H ₅ HHH OCH3 CH (CH ₃ )

3-84 4-C ₂ H ₅ HHH 0 CH3 CH (CH ₃ )

3-85 3-C ₃ H ₇ -i HHH 0CH3 CH (CH ₃ )

3-86 4-C3H ₇ -i HHH OCH3 CH (CH3)

3-87 3-C ₄ Hg-t HHH 0CH3 CH (CH ₃ )

3-88 4-C ₄ Hg-t HHH 0CH3 CH (CH ₃ )

3-89 3-OCH3 HHH 0CH3 CH (CH ₃ )

3-90 4-OCH3 HHH 0CH3 CH (CH ₃ ) (Table 38)

Compound χΐ X2 X3 A Melting point number (.C)

3-91 3-CF ₃ HHH 0CH ₃ CH (CH ₃ )

3-92 4-CF3 HHH OCH3 CH (CH ₃ ) 127-130

3-93 2.4-Cl ₂ HHH OCH3 CH (CH ₃ )

3-94 3, 4-Cl ₂ HHH OCH3 CH (CH ₃ )

3-95 3,5-Cl ₂ HHH OCH3 CH (CH ₃ )

3-96 3-CI, 4-FHHH OCH3 CH (CH ₃ )

3-97 3, 4- (CH ₃ ) ₂ HHH OCH3 CH (CH ₃ )

3-98 3, 5- (CH ₃ ) ₂ HHH OCH3 CH (CH ₃ )

3-99 3-OCF3 HHH OCH3 CH (CH ₃ )

3-100 4-OCF3 HHH OCH3 CH (CH ₃ )

3-101 HHHHH CH (C ₂ H ₅ ) 68-69

3-102 3-FHHHH CH (C ₂ H ₅ )

3-103 4-FHHHH CH (C ₂ H ₅ )

3-104 3-C1 HHHH CH (C ₂ H ₅ )

3-105 4- CI HHHH CH (C ₂ H ₅ )

3-106 3-CH3 HHHH CH (C ₂ H ₅ )

3-107 4-CH3 HHHH CH (C ₂ H) 79-82

3-108 4-C ₂ H ₅ HHHH CH (C ₂ H ₅ )

3-109 4-OCH3 HHHH CH (C ₂ H ₅ )

3-110 3- F3 HHHH CH (C ₂ H ₅ )

3-111 4- F3 HHHH CH (C ₂ H ₅ )

3-112 3.4-Cl ₂ HHHH CH (C ₂ H ₅ )

3-113 3, 5-Cl ₂ HHHH CH (C ₂ H ₅ )

3-114 3-CI, 4-FHHHH CH (C ₂ H ₅ )

3-115 3.4- (CH ₃ ) ₂ HHHH CH (C ₂ H ₅ )

3-116 3, 5- (CH ₃ ) ₂ HHHH CH (C ₂ H ₅ )

3-117 HHHHF CH (C ₂ H ₅ )

3-118 3-FHHHF CH (C ₂ H ₅ )

3-119 4-FHHHF CH (C ₂ H ₅ )

3-120 3-CI HHHF CH (C ₂ H ₅ )

3-121 4-CI HHHF CH (C ₂ H ₅ ) (Table 39)

Compound χΐ X ² X3 X4 A Melting point

(° C)

3-122 3-CH ₃ HHHF CH (C ₂ H ₅ )

3-123 4-CH3 HHHF CH (C ₂ H ₅ )

3-124 3-C ₂ H ₅ HHHF CH (C ₂ H ₅ )

3-125 4-C ₂ H ₅ HHHF CH (C2)

3-126 3-OCH3 HHHF CH (C ₂ H ₅ )

3-127 4-OCHQ HHHF CH (C ₂ H)

3-128 3- F3 HHHF CH (C ₂ H ₅ )

3-129 4-CF3 HHHF CH (C ₂ H ₅ )

3-130 2.4-Cl ₂ HHHF CH (C ₂ H ₅ )

3-131 3, 4-Cl ₂ HHHF CH (C ₂ H ₅ )

3-132 3,5-Cl ₂ HHHF CH (C ₂ H ₅ )

3-133 3-CI, 4- FHHHF CH (C ₂ H ₅ )

3-134 3, 4- (CH ₃ ) ₂ HHHF CH (C ₂ H ₅ )

3-135 3, 5- (CH ₃ ) ₂ HHHF CH (C ₂ H ₅ )

3-136 3-OCF3 HHHF CH (C ₂ H ₅ )

3-137 4-OCF3 HHHF CH (C ₂ H)

3-138 HHHH CI CH (C ₂ H ₅ )

3-139 3-FHHH CI CH (C ₂ H ₅ )

3-140 4-FHHH CI CH (C ₂ H ₅ )

3-141 3-CI HHH CI CH (C ₂ H ₅ )

3-142 4- CI HHH CI CH (C ₂ H ₅ )

3-143 3-CH3 HHH CI CH (C ₂ H ₅ )

3-144 4-CH3 HHH CI CH (C ₂ H ₅ )

3-145 3- C ₂ H ₅ HHH CI CH (C ₂ H ₅ )

3-146 4-C ₂ H ₅ HHH CI CH (C ₂ H ₅ )

3-147 3-OCH3 HHH CI CH (C ₂ H ₅ )

3-148 4-OCH3 HHH CI CH (C ₂ H ₅ )

3-149 3-CF3 HHH CI CH (C ₂ H ₅ )

3-150 4-CF3 HHH CI CH (C ₂ H ₅ )

3-151 2, 4-Cl ₂ HHH CI CH (C ₂ H ₅ )

3-152 3.4-Cl ₂ HHH CI CH (C ₂ H ₅ ) (Table 40

Compound Ym. \ 2 X3 X-5 A Melting point number (° C)

3-153 3, 5-Cl ₂ HHH CI CH (C ₂ H ₅ )

3-154 3-CI, 4-FHHH CI CH (C ₂ H ₅ )

3-155 3, 4- (CH ₃ ) ₂ HHH CI CH (C ₂ H ₅ )

3-156 3, 5- (CH ₃ ) ₂ HHH CI CH (C ₂ H ₅ )

3-157 3-0CF ₃ HHH CI CH (C ₂ H ₅ )

3-158 4-OCF3 HHH CI CH (C ₂ H ₅ )

3-159 HHHHH CH (C ₃ H ₇ )

3-160 4-FHHHH CH (C ₃ H ₇ )

3-161 4- CI HHHH CH (C ₃ H ₇ )

3-162 3-CH3 HHHH CH (C ₃ H ₇ )

3-163 -CH3 HHHH CH (C ₃ H ₇ )

3-164 4-OCH3 HHHH CH (C ₃ H ₇ )

3-165 3-CF3 HHHH CH (C ₃ H ₇ )

3-166 -CF3 HHHH CH (C ₃ H ₇ )

3-167 3, 4-Cl ₂ HHHH CH (C ₃ H ₇ )

3-168 3, 5-Cl ₂ HHHH CH (C ₃ H ₇ )

3-169 3.4- (CH ₃ ) ₂ HHHH CH (C ₃ H ₇ )

3-170 3.5- (CH ₃ ) ₂ HHHH CH (C ₃ H ₇ )

3-171 HHHHF CH (C ₃ H ₇ )

3-172 4-FHHHF CH (C ₃ H ₇ )

3-173 4-CI HHHF CH (C ₃ H ₇ )

3-174 3-CH3 HHHF CH (C ₃ H ₇ )

3-175 4-CH3 HHHF CH (C ₃ H ₇ )

3-176 4-C ₂ H ₅ HHHF CH (C ₃ H ₇ )

3-177 4-OCH3 HHHF CH (C ₃ H ₇ )

3-178 3-CF3 HHHF CH (C ₃ H ₇ )

3-179 4-CF3 HHHF CH (C ₃ H ₇ )

3-180 3.4-Cl ₂ HHHF CH (C ₃ H ₇ )

3-181 3, 5-Cl ₂ HHHF CH (C ₃ H ₇ )

3-182 3, 4- (CH ₃ ) ₂ HHHF CH (C ₃ H ₇ )

3-183 3, 5- (CH ₃ ) ₂ HHHF CH (C ₃ H ₇ ) (Table 41 :)

Compound Ym X2 X X4 A Melting point number (.c)

3-184 HHHH CI CH (C ₃ H ₇ )

3-185 4-FHHH CI CH (C ₃ H ₇ )

3-186 3-C1 HHH CI CH (C ₃ H ₇ )

3-187 4-C1 HHH CI CH (C ₃ H ₇ )

3-188 3-CH ₃ HHH CI CH (C ₃ H ₇ )

3-189 -CH ₃ HHH CI CH (C ₃ H ₇ )

3-190 4-OCHQ HHH CI CH (C ₃ H ₇ )

3-191 3-CF ₃ HHH CI CH (C ₃ H ₇ )

3-192 4- CF ₃ HHH CI CH (C ₃ H ₇ )

3-193 3, 4-Cl ₂ HHH CI CH (C ₃ H ₇ )

3-194 3, 5-Cl ₂ HHH CI CH (C ₃ H ₇ )

3-195 3, 4- (CH ₃ ) ₂ HHH CI CH (C ₃ H ₇ )

3-196 3, 5- (CH ₃ ) ₂ HHH CI CH (C ₃ H ₇ )

3-197 HHHHHC (CH ₃ ) ₂

3-198 3-FHHHHC (CH ₃ ) ₂

3-199 4-FHHHHC (CH ₃ ) ₂

3-200 3- CI HHHHC (CH ₃ ) ₂

3-201 4-CI HHHHC (CH ₃ ) ₂

3-202 3-CH ₃ HHHHC (CH ₃ ) ₂

3-203 -CH3 HHHHC (CH ₃₎ ₂

3-204 3-CF3 HHHHC (CH ₃ ) ₂

3-205 -CF3 HHHHC (CH ₃ ) ₂

3-206 3, 4-Cl ₂ HHHHC (CH ₃ ) ₂

3-207 3, 5-Cl ₂ HHHHC (CH ₃ ) ₂

3-208 3, 4- (CH ₃ ) ₂ HHHHC (CH ₃ ) ₂

3-209 3.5- (CH ₃ ) ₂ HHHHC (CH ₃ ) ₂

3-210 HHHHH CH ₂ CH ₂

3-211 3-FHHHH CH ₂ CH ₂

3-212 4-FHHHH CH ₂ CH ₂

3-213 3- CI HHHH CH ₂ CH ₂

3-214 4- CI HHHH CH ₂ CH ₂ (Table 4 2)

..9

Compound Ym X ¹ \ λ ⁴ A Melting point

(° C)

3-215 3-CH 0Q H H H H CH9CH

3-216 4- CH ₃ HHHH CH ₂ CH ₂

3-217 3-CF ₃ HHHH CH ₂ CH ₂

3-218 4-CF3 HHHH CH ₂ CH ₂

3-219 3, 4-Cl ₂ HHHH CH ₂ CH ₂

3-220 3, 5-Cl ₂ HHHH CH ₂ CH ₂

3-221 3, 4- (CH ₃ ) ₂ HHHH CH ₂ CH ₂

3-222 3, 5 (CH ₃ ) 2 HHHH CH ₂ CH ₂

(Table 43)

('Table 4 4)

Compound Ym X ¹ X2 X3 X4 R2 Melting point. (.C)

4-29 HH CI HH CH ₃

4-30 3- CI H CI HH CH ₃

4-31 4- CI H CI HH CH ₃

4-32 3-CH ₃ H CI HH CH ₃

4-33 4-CH3 H CI HH CH ₃

4-34 3, 4- (CH ₃ ) ₂ H CI HH CH ₃

4-35 3, 4-Cl ₂ H CI HH CH ₃

4-36 HH CI HH CH ₂ 0CH ₃

_{4-37 3- CI H CI HH CH 2} 0CH 3

4-38 4- CI H CI HH CH ₂ 0CH ₃

4-39 3-CH3 H CI HH CH ₂ 0CH ₃

4-40 -CH3 H CI HH CH ₂ 0CH ₃

4-41 3. 4- (CH ₃ ) ₂ H CI HH CH ₂₀ CH ₃

4-42 3, 4-Cl ₂ H CI HH CH ₂ 0CH ₃

4-43 HH CI HH CH ₂ CH = CH ₂

4-44 3-CI H CI HH CH ₂ CH = CH ₂

4-45 4- CI H CI HH CH ₂ CH = CH ₂

4-46 3-CH3 H CI HH CH ₂ CH = CH ₂

4-47 4-CH3 H CI HH CH ₂ CH = CH ₂

4-48 3. 4- (CH ₃ ) ₂ H CI HH CH ₂ CH = CH ₂

4-49 3, 4-Cl ₂ H CI HH CH ₂ CH = CH ₂

4-50 H H CI H H OCH3

4-51 3- CI H CI H H OCH3

4-52 4-CI H CI H H OCH3

4-53 3-CH3 H CI H H OCH3

4-54 4-CH3 H CI H H OCH3

4-55 3. 4- (CH ₃ ) ₂ H CI HH OCH3

4-56 3, 4-Cl ₂ H CI HH OCH3

4-57 HH 0CH3 HH CH ₃

4-58 3- CI H 0CH3 HH CH ₃

4-59 4-CI H 0CH3 HH CH ₃ (Table 45)

Compound Ym χΐ X2 X3 R2 Melting point

(° C)

4-60 -CH ₃ H 0CH ₃ HH CH ₃

4-61 4-CH3 H OCH3 HH CH ₃

4-62 3, 4- (CH ₃ ) ₂ H OCH3 HH CH ₃

4-63 3, 4-Cl ₂ H OCH3 HH CH ₃

4-64 HH OCH3 HH CH ₂ 0CH ₃

4-65 3- CI H OCH3 HH CH ₂ 0CH ₃

4-66 4-CI H OCH3 HH CH ₂ 0CH ₃

4-67 3-CH3 H OCH3 HH CH 2 0CH 3

_{4-68 4- H3 H OCH3 HH CH 2} 0CH 3

4-69 3, 4- (CH ₃ ) ₂ H OCH3 HH CH ₂ 0CH ₃

4-70 3, 4-Cl ₂ H OCH3 HH CH ₂ 0CH ₃

4-71 HH OCH3 HH CH ₂ CH = CH ₂

4-72 3-C1 H OCH3 HH CH ₂ CH = CH ₂

4-73 4- CI H OCH3 HH CH ₂ CH = CH ₂

4-74 3-CH3 H OCH3 HH CH ₂ CH = CH ₂

4-75 4-CH3 H 0CH ₃ HH CH ₂ CH = CH ₂

4-76 3, 4- (CH ₃ ) ₂ H OCH3 HH CH ₂ CH = CH ₂

4-77 3, 4-Cl ₂ H OCH3 HH CH ₂ CH = CH ₂

4-78 H H OCH3 H H OCH3

4-79 3-CI H OCH3 H H OCH3

4-80 4-CI H OCH3 H H OCH3

4-81 3-CH3 H OCH3 H H OCH3

4-82 -CH3 H OCH3 H H OCH3

4-83 3. 4- (CH ₃ ) ₂ H OCH3 HH OCH3

4-84 3, 4-Cl ₂ H OCH3 HH OCH3

4-85 HHHHF CH ₃

4-86 3- CI HHHF CH ₃

4-87 4- CI HHHF CH ₃

4-88 3-CH3 HHHF CH ₃

4-89 4-CH3 HHHF CH ₃

4-90 HHHF CH ₃ (Table 46)

(Table 4 7

Chemical compound Ym X ¹ X ² X3 X ⁴ R ² Melting point

(° C)

4-122 3- C ₂ H ₅ HHHF CH ₂ C≡CH

4-123 4- C ₂ H ₅ HHHF CH ₂ C≡CH

4-124 3-CF ₃ HHHF CH ₂ C≡CH

4-125 -CF3 HHHF CH ₂ C≡CH

4-126 3-OCH3 HHHF CH ₂ C≡CH

4-127 4-OCH3 HHHF CH ₂ C≡CH

4-128 3-0CFq HHHF CH ₂ C≡CH

4-129 4-OCF3 HHHF CH ₂ C≡CH

4-130 3. 4-Cl ₂ HHHF CH ₂ C≡CH

4-131 3, 4- (CH ₃ ) ₂ HHHF CH ₂ C≡CH

4-132 3, 5- (CH ₃ ) ₂ HHHF CH ₂ C≡CH

4-133 H H H H F OCH3

4-134 3-CI H H H F OCH3

4-135 4-CI H H H F OCH3

4-136 3- H3 H H H F OCH3

4-137 4- H3 H H H F O H3

4-138 3-C ₂ H ₅ HHHF OCH3

4-139 4- C ₂ H ₅ HHHF OCH3

4-140 3- F3 H H H F OCH3

4-141 4-CF3 H H H F OCH3

4-142 3-OCH3 H H H F OCH3

4-143 4-OCH3 H H H F OCH3

4-144 3-OCF3 H H H F OCH3

4-145 4-OCF3 H H H F OCH3

4-146 3, 4-Cl ₂ HHHF OCH3

4-147 3, 4-(CH ₃ ) ₂ HHHF OCH3

4-148 3, 5- (CH ₃ ) ₂ HHHF OCH3

4-149 HHHH CI CH ₃

4-150. 3-C1 HHH CI CH ₃

4-151 4-CI HHH CI CH ₃

4-152 3-CH3 HHH CI CH ₃ (Table 4 8)

(Table 49)

,

Compound X ² X ³ X ⁴ R ² Melting point number (.c)

4-184 3-CH ₃ HHH CI CH ₂ C≡CH

4-185 4- CH ₃ HHH CI CH ₂ C≡CH

4-186 3-C ₂ H ₅ HHH CI CH ₂ C three CH

4-187 -C ₂ H ₅ HHH CI CH ₂ C≡CH

4-188 3-CF3 HHH CI CH ₂ C≡CH

4-189 4-CF3 HHH CI CH ₂ C≡CH

4-190 3-OCHQ HHH CI CH ₂ C≡CH

4-191 4- OCH HHH CI CH ₂ C≡CH

4-192 3-0CFQ HHH CI CH ₂ C three CH

4-193 4-OCFQ HHH CI CH ₂ C≡CH

4-194 3. 4-Cl ₂ HHH CI CH ₂ C≡CH

4-195 3. 4- (CH ₃ ) ₂ HHH CI CH ₂ C≡CH

4-196 3.5- (CH ₃ ) ₂ HHH CI CH2C Three CH

4-197 H H H H CI OCH3

4-198 3-CI H H H CI OCH3

4-199 4- CI H H H CI OCH3 Oil

4-200 3-H3 H H H CI OCH3

4-201 4-CH3 H H H CI OCH3 oil

4-202 3-C ₂ H ₅ HHH CI OCH3

4-203 4-C ₂ H ₅ HHH CI OCH3

4-204 3-CF3 H H H CI OCH3

4-205 4-CF3 H H H CI OCH3

4-206 3-OCH3 H H H CI OCH3

4-207 4-OCH3 H H H CI OCH3

4-208 3-OCF3 H H H CI OCH3

4-209 4-OCF3 H H H CI OCH3

4-210 3. 4-Cl ₂ HHH CI OCH3

4-211 3. 4- (CH ₃ ) ₂ HHH CI OCH3

4-212 3, 5- (CH ₃ ) ₂ HHH CI OCH3

4-213 HHHH CH ₃ CH ₃

4-214 3- CI HHH CH ₃ CH ₃ (Table 50)

(: Table 51)

Compound Ym χΐ X ² X3 X4 R2 Melting point

(.C)

4-246 3-CI HHH CH ₃ CH ₂ C three CH

4-247 4- CI HHH CH ₃ CH ₂ C≡CH

4-248 3-CH ₃ HHH CH ₃ CH ₂ C≡CH

4-249 -CH3 HHH CH ₃ CH ₂ C three CH

4-250 3-C ₂ H ₅ HHH CH ₃ CH ₂ C≡CH

4-251 4-C ₂ H ₅ HHH CH ₃ CH ₂ C≡CH

4-252 3-CF3 HHH CH ₃ CH ₂ C≡CH

4-253 -CF3 HHH CH ₃ CH ₂ C≡CH

4-254 3-OCH3 HHH CH ₃ CH ₂ C≡CH

4-255 4-OCH3 HHH CH ₃ CH ₂ C≡CH

4-256 3-OCF3 HHH CH ₃ CH ₂ C≡CH

4-257 4-OCF3 HHH CH ₃ CH ₂ C≡CH

4-258 3, 4-Cl ₂ HHH CH ₃ CH ₂ C≡CH

4-259 3. 4- (CH ₃ ) ₂ HHHH ₃ CH ₂ C≡CH

4-260 3, 5- (CH ₃ ) ₂ HHH CH ₃ CH ₂ C 3 CH

4-261 HHHH CH ₃ OCH3

4-262 3- CI HHH CH ₃ OCH3

4-263 4- CI H H H OCH3

4-264 3-CH3 HHH CH ₃ OCH3

4-265 4-CH3 HHH CH ₃ OCH3

4-266 3-C ₂ H ₅ HHH CH ₃ OCH3

4-267 -C ₂ H ₅ HHH CH ₃ OCH3

4-268 3-CF3 HHH CH ₃ OCH3

4-269 4-CF3 HHH CH ₃ OCH3

4-270 3-OCH3 HHH CH ₃ OCH3

4-271 4-OCH3 HHH CH ₃ OCH3

4-272 3-OCF3 HHH CH ₃ OCH3

4-273 4-OCF3 H H H C¾ OCH3

4-274 3, 4-Cl ₂ HHH Cll ₃ OCH3

4-275 3, 4- (CH ₃ ) ₂ HHH CH ₃ OCH3

4-276 3, 5- (CH ₃ ) ₂ HHH CH ₃ OCH3 (Table 5 2

g 5 3) 1

Chemical compound Yra G Rl R2 Melting point number (.c)

6-1 I-CH3 0 CH ₃ H 84-86

6-2 6-OCH3 0 CH ₃ H

6-3 I -COCH3 0 CH ₃ H

0 u then rig n CH ₃ H

6-5 4-OCH3 0 CH ₃ H

6-6 H 0 CH ₃ H

6-7 H 0 CH ₃ CH ₃

6-8 H 0 H ₃ CH ₂ CH = CH ₂

6-9 H 0 CH ₃ CH ₂ C≡CH

6- 10 H 0 CH ₃ OCH3 A typical method for producing the biarylalkylenecarbamic acid derivative represented by the general formula [I], which is the compound of the present invention, is illustrated below.

Manufacturing method 1

[II] [I]

(In the formula, A, G, Q, R ¹ , R ² , X and n each have the same meaning as described above, and Z 1 represents a halogen atom.)

Compound [I] of the present invention can be produced by reacting compound [II] with compound [III] in an inert solvent in the presence of a base.

The amount of the starting compound used in this reaction is based on the compound [II].

[III] may be appropriately selected from the range of 0.5 to 3.0 equivalents, and preferably 0.8 to 1.5 equivalents.

The inert solvent that can be used in this reaction may be any solvent that does not hinder the progress of this reaction, and examples thereof include ketones such as acetone, methylethylketone and cyclohexanone, getyl ether, and diisopropyl ether. Ethers such as tetrahydrofuran, dioxane, monoglyme, and diglyme; esters such as ethyl acetate and methyl acetate; halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride, and tetrachlorene ethane Aromatic hydrocarbons such as benzene, benzene, benzene, nitrobenzene, and toluene; nitriles such as acetonitrile; N, N-dimethylformamide; N, N-dimethylacetamide; —Dimethyl-2-imidazolinone, dimethyl sulfoxide, etc. can be used. Medium may be used alone or in combination.

As the base used in this reaction, an inorganic base or an organic base can be used. Examples of the inorganic base include sodium carbonate, lithium carbonate, calcium carbonate, sodium hydrogencarbonate, sodium hydroxide, sodium hydroxide, water, and water. Such as calcium oxide A hydride of an alkali metal atom such as a carbonate or hydroxide of a alkali metal or alkali earth metal atom, lithium hydride, or sodium hydride can be used. For example, triethylamine, disopropyrethylamine, pyridine and the like can be used. These bases can be used alone or in combination. ] May be appropriately selected from the range of 0.5 to 3.0 equivalents, and preferably 0.8 to 2.0 equivalents. The reaction temperature may be selected from the boiling point range of the inert solvent used after -70, and preferably in the range of 40 ° C to 40 ° C. The reaction time is not fixed depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of several minutes to 48 hours. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method, and if necessary, purified by column chromatography, recrystallization, or the like. Manufacturing method 2

[II] [I-1]

(In the formula, A, QR ¹ , R ² , X and η each have the same meaning as described above.) The present invention is obtained by reacting the compound [II] with the compound [IV] in an inert solvent. Compound [1-1] can be produced.

The amount of the starting compound used in this reaction may be appropriately selected from the range of 0.5 to 3.0 equivalents of compound [IV] relative to compound [II], and preferably 0.8 to 2.0 equivalents. It is.

As the inert solvent that can be used in this reaction, the solvents exemplified in Production Method 1 can be used.

The reaction temperature may be selected from the range of 170 ° C. to the boiling point of the inert solvent used, and is preferably in the range of −10 ° C. to the boiling point of the inert solvent. The reaction time is not fixed depending on the reaction temperature, reaction amount, etc., but is generally selected from the range of several minutes to 48 hours. do it. After completion of the reaction, the desired product is isolated from the reaction system by a conventional method, and if necessary, purified by column chromatography, recrystallization, or the like.

Manufacturing method 3

(In the formula, A, G, Q, R1, R2, X and n each have the same meaning as described above, and Z2 represents a chlorine atom, a bromine atom, an iodine atom, a tosyloxy group or a mesyloxy group.)

Compound [V] of the present invention can be produced by reacting compound [V] with compound [VI] in an inert solvent in the presence of a base.

The amount of the starting compound used in this reaction may be appropriately selected from the range of 0.5 to an excess equivalent of the compound [VI] with respect to the compound [V], and is preferably 0.8 to 2.0 equivalents. .

As the base used in this reaction, the bases exemplified in Production Method 1 can be used. The amount of the base to be used may be appropriately selected from the range of 1 equivalent to excess equivalent relative to compound [V], and is preferably in the range of 1 equivalent to 2 equivalents.

The reaction temperature may be selected from the range of from 170 ° C. to the boiling point of the reaction mixture used, and preferably from 110 ° C. to the boiling point of the reaction mixture. The reaction time is not fixed depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of several minutes to 48 hours. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method, and if necessary, purified by column chromatography, recrystallization, or the like. Manufacturing method 4

(In the formula, A, G, Q, scale ¹ , X and n each have the same meaning as described above.) The compound of the present invention is obtained by reacting compound [VII] with compound [VIII] in an inert solvent. [1-2] can be manufactured.

The amount of the starting compound used in this reaction may be appropriately selected from the range of 1 equivalent to excess equivalent of compound [VIII] with respect to compound [VIII], and is preferably 1.0 to 2.0 equivalents.

The reaction temperature may be selected from the range of −70 ° C. to the boiling point of the reaction mixture used, preferably from 110 ° C. to the boiling point of the reaction mixture. The reaction time is not constant depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of several minutes to 48 hours. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method, and if necessary, purified by column chromatography, recrystallization, or the like. Manufacturing method 5

(Wherein, A, G, Q, R ¹ X and n each have the same meaning as described above, and R ^ ′ has the same meaning as R ² (which has the same meaning as described above) except for a hydrogen atom. 2 represents a chlorine atom, a bromine atom, an iodine atom, a tosyloxy group or a mesyloxy group.) The compound of the present invention [1-3] can be produced by reacting the compound of the present invention [1-2] with the compound [IX] in an inert solvent in the presence of a base.

The amount of the starting compound used in this reaction may be appropriately selected from the range of 1 equivalent to excess equivalent of the compound [IX] based on the compound [I-12] of the present invention, and is preferably 1.0 to 3. It is 0 equivalent.

As the base used in this reaction, the bases exemplified in Production Method 1 can be used. The amount of the base to be used may be appropriately selected from the range of 1 equivalent to excess equivalent relative to compound [1-2], and is preferably in the range of 1 equivalent to 2 equivalents.

The reaction temperature may be selected from -70 ^S C in the boiling range of the inert solvent used. The reaction time is not fixed depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of several minutes to 48 hours. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method, and if necessary, purified by column chromatography, recrystallization, etc. Manufacturing method 6

[X] [i]

(In the formula, A, G, Q, R ¹ R ² , X and n each have the same meaning as described above, and Z 3 represents a bromine atom, an iodine atom or a trifluoromethanesulfonyloxy group. :)

A known method of reacting compound [X] with compound [XI] in the presence of a zero-valent palladium catalyst [XII] and a base in an inert solvent (for example, Synthetic)

The compound [I] of the present invention can be produced according to the method described in Communicats, Vol. 11, page 513 (1981).

The amount of the starting compound used in this reaction is compound [XI] to compound [XI] May be appropriately selected from the range of 1 equivalent to excess equivalent, and preferably in the range of 1 equivalent to 2 equivalents.

The solvent that can be used in this reaction is not limited as long as it does not inhibit the progress of this reaction.Examples include ethers such as getyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme, diglyme, benzene, and Mouth Aromatic hydrocarbons such as benzene, nitrobenzene, and toluene; nitriles such as acetonitrile; methanol, ethanol, and chlorobenzene. Alcohols such as ethanol, 2-propanol, esters such as methyl acetate and ethyl acetate, NN-dimethylformamide, NN-dimethylacetamide, water, etc., and these solvents can be used alone or It can be mixed and used.

Tetrakis (triphenylphosphine) is a zero-valent palladium catalyst that can be used in this reaction. Radium (0), bis (dibenzylideneacetone) ,. A palladium complex such as radium (0) or tris (dibenzylideneacetone) dipalladium (0) can be used, and the amount used is in the range of 0.01 to 1 equivalent to the compound [X]. It may be appropriately selected, and preferably in the range of 0.01 equivalent to 0.2 equivalent.

Bases used in this reaction include sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, potassium hydroxide, potassium hydroxide, and other alkali metal atoms. Alternatively, a carbonate or hydroxide of an alkaline earth metal atom can be used, and these bases can be used alone or in combination. The amount of the base used is based on the compound [X]. The reaction temperature may be selected from the range of 1 to 2 equivalents, preferably the range of 1 to 2 equivalents, and the reaction temperature may be selected from 100 ° C. to the boiling point range of the inert solvent used. Preferably, the reaction is carried out in the range from room temperature to the boiling point of the reaction mixture. The reaction time is not fixed depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of several minutes to 48 hours. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method, and if necessary, purified by column chromatography, recrystallization, or the like.

The boric acid derivative of the compound [XI] can be produced by a known method (for example, Experimental Chemistry Lecture, 4th edition, Vol. 24, p. 80, Maruzen). Manufacturing method 7

[V] [1-2]

(In the formula, A, G, Q, R 丄, X, n, and Z each have the same meaning as described above, and M represents a sodium atom or a force atom.)

The compound [1-2] of the present invention can be produced by reacting compound [V] with compound [XIII] and compound [VIII] in an inert solvent.

The amount of the starting compound used in this reaction is the amount of compound [V]

[XIII] may be appropriately selected from the range of 1.0 to 5.0 equivalents, preferably 1.0 to 3.0 equivalents, and compound [VIII] is 1.0 to 5.0 equivalents to compound [V]. L, should be appropriately selected from the range of excess equivalent.

The reaction temperature may be selected from the room temperature to the boiling point range of the reaction mixture to be used, preferably from 30 ° C. to the boiling point of the reaction mixture. The reaction time is not fixed depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of 1 hour to 24 hours. After completion of the reaction, the desired product is isolated from the reaction system by a conventional method, and if necessary, purified by column chromatography, recrystallization, etc.

Method for producing compound [II]

The compound [Ι される is synthesized, for example, according to the following methods a to d, but the method is not limited thereto.

(Method a)

[xiv] [Π] (Wherein, A, Q, R ² , X, n, and Z 3 each have the same meaning as described above.) According to the above-mentioned Production Method 6, compound [XIV: and compound [XI] are compounded with compound [XII ] And a base in the presence of an inert solvent to give compound [II].

(Method b)

[XVII]

(In the formula, Q, R ² , X, n and Z ³ each have the same meaning as described above, and A ′ represents an optionally branched (C i -C ₆ ) alkylene group or a bond.)

After reducing the compound [XV], the obtained compound [XVI] is reacted in an inert solvent in the presence of the compound [XI], the compound [XII] and a base according to the above-mentioned Production Method 6. Compound [I 1-1] can be produced.

Compound [XV] is reacted with compound [XI] in the presence of compound [XII] and a base in an inert solvent according to the above-mentioned Production method 6, and then the obtained compound [XV II] is reduced. By doing so, compound [II-1] can be produced. (Method c

[XX]

(In the formula, A ′, Q, X, n and Z 3 each have the same meaning as described above.) After reducing the compound [XV III], the obtained compound [XIX] was purified according to the above-mentioned Production Method 6. Then, compound [I1-2] can be produced by reacting compound [XI] with compound [XII] and a base in an inert solvent. Further, after reacting compound [XVIII] with compound [XI] in the presence of compound [XII] and a base in an inert solvent according to the above-mentioned Production method 6, the obtained compound [XX] ] To produce compound [I 1-2].

(Method

(In the formula, Q, X, n and Z 3 each have the same meaning as described above, and R 6 represents an alkyl group.)

A compound obtained by reductive amination of compound [XXI] or reacting compound [XXI] with hydroxylamine hydrochloride in an inert solvent and then reducing the resulting compound [XXII] [XXIII] was converted to a compound according to Production Method 6 described above.

Compound [I1-3] can be produced by reacting [XI] with compound [Χ] and a base in an inert solvent. Method for producing compound [V]

[XXV] [V]

, Logenification, mesylation

Or tosylation

[XXVI]

(Wherein, A, Q, X, ri and Z 2 each have the same meaning as described above.) Compound [V] is a halogenated compound [XXV] or a halogenated or mesylated compound [XXV I]. Alternatively, it can be produced by tosylation. Method for producing compound [V I I]

[XXIV] [VII] (Wherein, A, Q, X and n each have the same meaning as described above.) Compound [VII] can be produced by a known method (for example, Shin-Jikken Kagaku Koza, Vol. 14, page 1490, Maruzen). can do. Method for producing compound [X]

Compound [X] can be produced according to Production Method 1 to 5 or Production Method 7 as a compound of the general formula [I] wherein Q is Z3.

[Best Mode for Carrying Out the Invention]

Next, the production method, formulation method and use of the compound of the present invention will be specifically described with reference to examples. Production Example 1 Production of methyl N- (3-phenylpentyl) caprate (Compound No. 11-1)

3-Phenylbenzylamine 11.24 g of pyridine was added to a toluene (250 m) solution of 11.18 g at room temperature. To this solution, 9.58 g of methyl chloroformate was added dropwise with stirring under ice-cooling, and the mixture was returned to room temperature and stirred for 2 hours. After completion of the reaction, the reaction solution was poured into an aqueous solution of citric acid, extracted with ethyl acetate, the organic layer was washed with an aqueous solution of citric acid, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 8.61 g of methyl N- (3-phenylbenzyl) acetate as pale yellow crystals. Melting point 49-52 ° C

1 H-NMR: (CDC 1 3 / TMS, δ (p pm)) 3. 70 (s, 3H), 4. 43 (d, 2 H), 5. 06 (br, 1 H), 7. 1 6-7.59 (m, 9H) Preparation Example 2 Preparation of methyl N- [3- (3,4-dichlorophenyl) benzyl] caprate (Compound No. 1-118)

N-(: 3-bromobenzyl) carbami in toluene (40ml) under nitrogen atmosphere An aqueous solution (20 ml) of 1.30 g of methyl phosphate, 0.56 g of sodium carbonate and 0.13 g of tetrax (triphenylphosphine) palladium (0) were added. Under stirring at room temperature, a solution of 1.02 g of 3,4-dichlorophenylboric acid in ethanol (20 ml) was added to the solution, and the mixed solution was refluxed for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature, poured into a saturated saline solution, extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.45 g of methyl N- [3- (3,4-dichloromouth phenyl) benzyl] carbamate as a yellow transparent viscous liquid.

_{1 H- MR: (CDC 1 3} / TMS, o (p pm)) 3. 69 (s, 3H), 4. 4 0 (d, 2 H), 5. 2 3 (br, 1 H), 7 25-7.63 (m, 7H) Production Example 3 Production of isopropyl N- (3-phenylbenzyl) carbamate (Compound No. 1-150)

Under a nitrogen atmosphere, an aqueous solution (20 ml) of 1.20 g of N- (3-bromobenzyl) isopropyl carbamate and 0.47 g of sodium carbonate in toluene (40 ml) and tetrakis (triphenylphosphine) 0.10 g of palladium (0) was added. Under stirring at room temperature, a solution of 0.54 g of phenylboric acid in ethanol (20 ml) was added to the solution, and the mixed solution was refluxed for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature, poured into a saturated saline solution, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.85 g of isopropyl N- (3-phenylbenzyl) carbamate as white crystals. Melting point 6 1 to 64 ° C

1 H-NMR: (CDC 1 3 / TMS, δ (p pm)) 1. 24 (d, 6H), 4. 43 (d, 2 H), 4. 95 (br, 1 H), 4. 96 (m, 1H), 7.26-7.59 (m, 9H) Production Example 4 N- (3-phenylbenzyl) -N- (2-propynyl) carpa'min Of Methyl Oxalate (Compound No. 1-178)

To a solution of 0.70 g of methyl N- (3-phenylbenzyl) carbamate in 20 ml of tetrahydrofuran (0.10 g) was added 0.15 g of 60% sodium hydride at room temperature. And stirred for 30 minutes. To this solution was added dropwise 0.52 g of propargylbutane at room temperature, and the mixture was stirred overnight. After completion of the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel gel chromatography to obtain 0.54 g of N- (3-phenylbenzyl) N- (2-propynyl) methyl methylbamate as a yellow transparent viscous liquid. .

_{1 H- MR: (CDC 1 3} ZTMS, 6 (ppm)) 2. 2 4 (t, 1 H),

3.79 (s, 3H), 3.99-4.10 (m, 2H), 4.67 (s, 2H), 7.25-7.59 (m, 9 H) Preparation Example 5 Preparation of N-methoxymethyl-N- (3-phenylbenzyl) methyl methylbamate (Compound No. 1-192)

To a solution of 1.0 g of methyl N- (3-phenylbenzyl) carbamate in 20 ml of tetrahydrofuran (20 ml) was added 0.22 g of 60% sodium hydride at room temperature. Stirred for 0 minutes. 0.78 g of methoxymethyl bromide was added dropwise to this solution at room temperature, and the mixture was stirred overnight. After completion of the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the organic layer was separated, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.90 g of N-methoxymethyl-1-N- (3-phenylbenzyl) methyl methylbamate as a pale yellow transparent viscous liquid.

¹ H-NMR: (CDC 13 / TM S, δ (ppm)) 3.29-3.34 (m, 3 H), 3.77 (s, 3 H), 4.48- 4.6 2 (d el, 2 H),

4.66—4.78 (dd, 2H), 7.06—7.58 (m, 9H) Preparation 6 N- (2-Methyl-3-phenylbenzyl) caprate Production of methyl (Compound No. 2-1) 3.57 g of 2-methyl-1-phenylbenzyl bromide, 1.66 g of potassium cyanate and 7.00 g of methanol, N, N-dimethylformamide ( The 30 mD solution was stirred for 5 hours at 80 ° C. After the reaction was completed, the reaction solution was poured into water, extracted with ethyl acetate, the organic layer was separated, dried over anhydrous magnesium sulfate, and then dried under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography, and methyl N- (2-methyl-3-phenylphenyl) carbamate was added.

2.0 g was obtained as colorless crystals. Melting point 9 1 to 94 ° C

1 H-NMR: (CDC 1 3 / TMS, δ (p pm)) 2. 20 (s, 3H),

3.7 1 (s, 3H), 4.43 (d, 2H), 5.24 (br, 1H :), 7.2-7.4 (m, 8H) Production example 7 N- {1 -[3- (4-Methoxyphenyl) phenyl] ethyl} Production of methyl carbamate (Compound No. 3-15)

Under a nitrogen atmosphere, an aqueous solution of toluene (40 ml) in N- [1- (3-promophenyl) ethyl] methylbamate 1.0 g, sodium carbonate 0.41 g

(20 ml) and 0.09 g of tetrax (triphenylphosphine) norradium (0) were added. Under stirring at room temperature, a solution of 0.59 g of 4-methoxyphenylboric acid in ethanol (20 ml) was added to the solution, and the mixed solution was refluxed for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature, poured into a saturated saline solution, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and N— {1-[3—

(4-Methoxyphenyl) phenyl] methylcarbamate 1.45 g was obtained as pale yellow crystals. Melting point 1 17 ~ 1 19 ° C

¹ H-NMR: (CDC 13 / MS, δ (ρ pm)) 1.5 1 (d, 3Η), 3.66 (s, 3Η), 3.84 (s, 3H), 4.89 ( br, 1 H), 4.99 (br, 1 H), 6.94-7.52 (m, 8 H) Production Example 8 N-Methoxy-1-N- (2-methyl-3-phenylphenyl) Production of methyl carbamate (Compound No. 4-1 22) 0.18 g of 60% sodium hydride was added to a solution of 40 g of methyl N-methoxycarbamate at room temperature in a solution of 40 g of N, N-dimethylformamide (20 ml), followed by stirring for 30 minutes. To this solution, 1.00 g of 2-methyl-3-phenylpentyl bromide was added dropwise at room temperature, and the mixture was stirred for 3 hours. After completion of the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the organic layer was separated, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.55 g of N-methoxy-1-N- (2-methyl-3-phenylbenzyl) methyl methylbamate as a transparent viscous liquid.

1 H-NMR: (CDC 13 / TMS, <5 (p pm)) 2.23 (s, 3H), 3.55 (s, 3H), 3.83 (s, 3H), 4.75 (s, 2H :), 7.2-7.5 (m, 8H)

Then, some of the ¹ H of the embodiment of the present invention compounds _{- NMR (CDC 1 3 Z TMS} , δ (p pm)) showing the data.

89: ''

¾ν1υ o-1.

¾ 9 S

i]) α

s 6

G

G

s

—

(9H ^ 2. (Table 57) Compounds

! H-NMR (5 value (ppm) solvent CDC1 ₃

2-123 3.68 (s, 3H); 3.86 (s, 3H); 4.46 (d.2H); 5.14 (br, IH); 6.89 (dd, IH); 7.04-7.53 (m, 6H)

2-125 3.70 (s, 3H); 4.47 (d, 2H); 5.15 (br, IH); 7.10-7.55 (ra, 7H)

2-126 3.69 (s, 3H); 4.46 (d, 2H); 5.21 (br, IH); 6.9-7.5 (m, 7H)

2-166 2.29 (s, 3H); 2.32 (s, 3H); 3.68 (s, 3H); 4.45 (d, 2H); δ.17 (br, IH); 7.00 (t, IH); 7.1-7.6 (m, 5H)

2-185 3.68 (s, 3H); 4.48 (dd, 2H); 5.21 (br, IH); 7.22-7.46 (m, 7H)

2-186 3.69 (s, 3H); 4.49 (d.2H); 5.29 (br. IH); 7.33-7.58 (m, 7H)

2-188 2.24 (s, 3H); 3.66 (s, 3H); 4.49 (d, 2H); 5.25 (br, IH); 7.16-7.51 (in, 7H)

2-189 2.41 (s, 3H); 3.68 (s, 3H); 4.50 (d, 2H); 5.26 (br, IH); 7.08-7.59 (m, 7H)

2-191 1.8 (t, 3H); 2.72 (q, 2H); 3.69 (s, 3H); 4.51 (d, 2H); 5.21 (br, IH); 7.21-7.60 (m, 7H)

2-193 1.29 (d, 6H); 2.97 (sept, IH); 3.68 (s, 3H): 4.50 (d, 2H); 5.25 (br, IH); 7.25-7.59 (m, 7H)

2-196 1.36 (s, 9H); 3.69 (s, 3H); 4.51 (d, 2H); 5.19 (br, IH); 7.39-7.60 (in, 7H)

2-284 2.36 (s, 3H); 3.69 (s, 3H); 4.42 (d, 2H); 4.94 (br, 1H); 7.22-7.57 (m, 8H)

2-333 2.41 (s, 3H); 3.67 (s, 3H); 3.88 (s, 3H); 4.41 (d, 2H); 5.25 (br, IH); 6.92 (d, IH); 7.13-7.50 (ra , 6H) (Table 58) Compounds

! H-MR 5 value (ρρι) Solvent CDC1 ₃

2-346 2.29 (s, 3H); 3.32 (s, 3H); 3.67 (s, 3H); 3.88 (s.3H); 4.41 (d, 2H);

5.24 (br, 1H); 6.92 (d, 1H); 7.16-7.48 (m, 5H)

2-448 3.70 (s, 3H); 4.49 (d, 2H); 5.40 (br, 1H); 6.32 (br, 1H); 6.83-7.56 (m, 7H)

3-1 1.51 (d, 3H); 3.65 (s, 3H); 4.91 (m, 1H); 5.09 (br, 1H); 7.1δ-7.72 (m, 9H)

3-6 1.50 (d, 3H); 2.41 (s, 3H); 3.65 (s, 3H); 4.90 (br, 1H); 5.12 (br, 1H);

7.1-7.5 (m, 8H)

3-16 1.52 (d, 3H); 3.66 (s, 3H); 4.91 (br, 1H); 5.14 (br, 1H); 7.1-7.8 (m, 8H)

3-18 1.51 (d, 3H); 3.66 (s, 3H); 4.90 (br, 2H); 7.3-7.5 (m, 7H)

3-20 1.49 (d, 3H); 3.65 (s, 3H); 4.89 (br, 1H); 5.24 (br, 1H); 7.3-7.4 (m, 7H)

3-26 1.53 (d, 3H); 3.66 (s, 3H); 5.07 (q, 1H); 5.19 (br, 1H); 7.10 (dd, 8H);

7.31-7.54 (m, 7H)

4-199 3.65 (s, 3H); 3.83 (s, 3H); 4.86 (s, 2H); 7.38-7.53 (m, 7H)

4-201 2.39 (s, 3H); 3.63 (s, 3H); 3.82 (s, 3H); 4.85 (s, 2H); 7.22-7.57 (m, 7H)

Next, Production Examples of the synthetic intermediate of the compound of the present invention will be shown as Reference Examples. Reference Example 1 Production of methyl N- (3-bromobenzyl) carbamate

9.55 g of triethylamine was added to a suspension of 1-0.00 g of 3-bromobenzylamine hydrochloride in 100 ml of chloroform in room temperature at room temperature. 4.67 g of methyl chloroformate was added dropwise to this solution with stirring under ice cooling, and the mixture was returned to room temperature and stirred for 2 hours. After completion of the reaction, the reaction solution was poured into a saturated saline solution, the organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off under normal pressure. The residue is purified by silica gel column chromatography. F7

It was isolated and purified by filtration to give 9.54 g of methyl N- (3-bromobenzyl) potamate as white crystals. Melting point 4 1 ~ 4 4

_{1 H- MR: (CDC 1 3} / MS, o (ppm)) 3. 6 9 (s, 3 H), 4. 3 3 (cl, 2 H), 5. 1 7 (br, 1 H), 7.16—7.42 (m, 4H) Reference Example 2 Production of isopropyl N- (3-bromobenzyl) phosphate

To a suspension of 3.0 g of 3-bromobenzylamine hydrochloride in 20 ml of chloroform (20 ml) was added 2.86 g of triethylamine at room temperature. 1.82 g of isopropyl chloroformate was added dropwise to this solution with stirring under ice-cooling, and the mixture was returned to room temperature and stirred for 2 hours. After completion of the reaction, the reaction solution was poured into saturated saline, the organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off under normal pressure. The residue was isolated and purified by silica gel column chromatography to obtain 3.33 g of isopropyl N- (3-bromobenzyl) -caprate as a colorless transparent viscous liquid.

. 1 H - NMR: (CDC 1 3 ZT MS, δ (ppm)) 1 2 4 (d, 6 H), 4. 3 2 (d, 2 H), 4. 9 6 (m, 1 H), 5-0 2 (br, 1H), 7.16-7.43 (m, 4H) Reference Example 3 Production of 3-phenylpentylamine

Under a nitrogen atmosphere, an aqueous solution of 12.25 g of 3-bromobenzylamine hydrochloride and 17.39 g of sodium carbonate in toluene (240 ml) (120 m m) and tetraura 1.90 g of kiss (triphenylphosphine) palladium (0) was added. Under stirring at room temperature, a solution of 10.0 g of phenylboric acid in ethanol (120 ml) was added to this solution, and the mixed solution was heated to reflux for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature, poured into a saturated saline solution, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. As a crude product, 11.18 g of 3-phenylbenzylamine as a brown viscous liquid was obtained. Reference Example 4 Production of methyl N- [1— (3-promophenyl) ethyl] carbamate F 8

Construction

3 — Bromone methinobenzoylamine 2 To 4.77 g of a solution of toluene (120 ml) was added 14.08 g of pyridine at room temperature. To this solution, 18.64 g of methyl chloroformate was added dropwise with stirring under ice cooling, and the mixture was returned to room temperature and stirred for 2 hours. After completion of the reaction, the reaction solution was poured into an aqueous solution of citrate, extracted with ethyl acetate, the organic layer was washed with an aqueous solution of citrate, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was isolated and purified by silica gel gel chromatography to obtain 10.50 g of N- [1- (3-bromophenyl) ethyl] methyl lvaminate as a colorless transparent viscous liquid.

1 H-NMR: (CDC 1 3 / TMS, δ (p pm)) 1. 46 (d, 3H), 3. 65 (s, 3 H), 4. 78 (br, 1 H), 5. 1 4 (br, 1H), 7. 16-7.42 (m, 4H) Reference Example 5 Production of methyl N-methoxy-1-N- (3-bromobenzyl) carbamate

To a solution of methyl N-methoxycarbamate 2.528 in ^^, N-dimethylformamide (30 ml) was added 1.15 g of 60% sodium hydride at room temperature, and the mixture was stirred for 30 minutes. To this solution, 1.00 g of 3-bromobenzyl bromide was added dropwise at room temperature, and the mixture was stirred for 3 hours. After completion of the reaction, the reaction solution was poured into water, extracted with ethyl acetate, the organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4.99 g of methyl N-methoxy-N- (3-bromobenzyl) caprate as a clear viscous liquid. ·

1 H-NMR: (CDC 13 / TMS, δ (ppm)) 3.62 (s, 3H), 3.81 (s, 3H), 4.61 (s, 2H), 7.0 -7.6 (m, 4 H) The agricultural / horticultural fungicide of the present invention contains a biarylalkylenecarbamic acid derivative represented by the general formula [I] as an active ingredient. When the compound of the present invention is used as an agricultural and horticultural fungicide, the active ingredient should be used in an appropriate dosage form according to the purpose. Can be. Usually, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant and other substances can be added to the active ingredient for use in the form of powders, wettable powders, emulsions, granules, and the like.

Suitable carriers include, for example, solid carriers such as talc, bentonite, cres, kaolin, diatomaceous earth, white carbon, permikilite, slaked lime, silica sand, ammonium sulfate, urea, isopropyl alcohol, xylene, cyclohexanone, And liquid carriers such as methylnaphthalene. Examples of surfactants and dispersants include dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, and polyoxyethylene alkylaryl. Ether, polyoxyethylene sorbitan monoalkylate and the like can be mentioned. Examples of the auxiliary include carboxymethylcellulose and the like. These preparations are diluted to an appropriate concentration and sprayed or applied directly.

The fungicide for agricultural and horticultural use of the present invention can be used by foliage application, soil application or water surface application. The compounding ratio of the active ingredient is appropriately selected according to need, but it is 0.1 to 20% (by weight) for powders and granules, and 5 to 20% for emulsions and wettable powders.

80% (weight) is appropriate.

The application rate of the agricultural and horticultural fungicide of the present invention varies depending on the type of the compound used, the target disease, the tendency to occur, the degree of damage, the environmental conditions, the dosage form used, and the like. For example, when used as is, such as powders and granules, the active ingredient should be added at 0.

It is appropriate to appropriately select from the range of 1 g to 5 kg, preferably 1 g to 1 kg. In addition, when used in liquid form, such as antifoaming agents and wettable powders, 0.1 lpm to 10

It is appropriate to appropriately select from O O O ppm, preferably from the range of 10 to 3,000 ppm.

The compound according to the present invention can control plant diseases caused by algal fungi (Oomycetes), fungi (Ascomycetes), incomplete fungi, (Deuteromycetes), and basidiomycetes (Basidiomycetes) by the above-mentioned application forms. . Next, specific bacterial names are given as non-limiting examples. The genus Pseudoperonospora, Pseudoperonospora cubensis, and the genus Pseudoperonospora cubensis Genus (Erysiphe), for example, Erysiphe graminis, Venturia, for example, Venturia inaequalis :, Pyricularia, for example, Pyricularia oryzae ) ヽ A genus of Botrytis (eg, Botrytis cinerea), a genus of Rhizoctonia (eg, Rhizoctonia solani).

Further, the compound of the present invention may be mixed with an insecticide, other fungicides, herbicides, plant growth regulators, fertilizers and the like, if necessary. Next, the formulation method will be specifically described with reference to typical examples of the agricultural and horticultural fungicides of the present invention. In the following description, “%” indicates weight percentage. Formulation Example 1 Powder

2% of the compound (2-102), 5% of diatomaceous earth and 93% of cre-93 were uniformly mixed and pulverized to obtain a powder.

Formulation Example 2 wettable powder

50% of the compound (1-12), 45% of diatomaceous earth, 2% of sodium dinaphthylmethanedisulfonate and 3% of sodium ligninsulfonate were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 3 Emulsion

Compound (114) 30%, cyclohexanone 20%, polyoxyethylene alkylaryl ether 11%, calcium alkylbenzenesulfonate 4% and methylnaphthalene 35% are uniformly dissolved. An emulsion was prepared.

Formulation Example 4 Granules

5% of compound (1-1), 2% of sodium salt of lauryl alcohol sulfate, 5% of sodium ligninsulfonate, 2% of carboxymethylcellulose and 86% of clay are uniformly mixed and pulverized. The mixture was kneaded by adding an amount of water equivalent to 20%, processed into granules of 14 to 32 mesh using an extrusion granulator, and then dried to obtain granules. Next, the effect of the agricultural and horticultural fungicide of the present invention will be specifically described with reference to test examples. You. Test example 1

Nine cucumber seeds (variety: Sagami Hanjiro) were sowed in each 9 cm x 9 cm PVC pot and cultivated in a greenhouse for 7 days. A wettable powder prepared in accordance with Formulation Example 2 was diluted with water to make the active ingredient 500 ppm by water, and 10 ml per pot was sprayed on the seedlings of Cucurbita with cotyledons developed. After air-drying, zoosporangium and a suspension of zoospores of Pseudoperonospora cubensis were sprayed and inoculated, and immediately placed in a moist chamber at 22 ° C for 24 hours. After that, they were transferred to a greenhouse, and the diseased area of the entire pot was investigated 7 days after inoculation, and evaluated based on the criteria in Table 59. The results are shown in Tables 60 to 61.

(Table 59) Evaluation control

A We do not notice the onset

B 25 Less than 5% affected area

C 2 5% or more and less than 50%

D 50% or more affected area

(Table 60) Compound number Evaluation

1 3 A

1 1 7 B

1-1 1 A

1-1 2 B

1-33 B

1-34 A

1 to 4 1 A

1-1 03 B

1-1 1 8 B

1-1 1 9 B

1-1 25 A

1-178 B

1 -253 B

1-266 B

2-9 1 B

2- 98 B

2-102 A

2-1 06 A

2-1 07 A

2-1 09 A

2-1 1 0 A

2- 1 1 1 A

2- 1 1 3 B

2- 1 2 1 A

2- 1 22 B

2- 1 23 A

2-1 26 B

2-1 83 A

2- 1 84 B

2-1 86 B

2-1 89 B

2-1 9 1 A (Table 6 1.) Compound number Evaluation

2-1 9 3 A

2-201 A

2-2 0 3 B

2-205 A

2-2 1 5 A

2-24 6 B

2-24 7 B

2-2 5 7 B

2-2 6 6 B

2-2 6 8 A

2-2 8 8 A

2-290 A

2-2 9 9 A

2-3 0 0 B

2-3 2 8 A

2-3 3 1 A

2-3 3 3 A

2-3 34 B

2-3 4 3 A

2-34 6 B

2-4 5 0 A

3 1 1 A

3-6 A

3-15 A

3-16 A

3-2 1 A Test example 2 Apple scab prevention effect test

9 cm>: Five apple seeds (variety: Kodama) were sown in 9 cm PVC pots and grown in a greenhouse for 20 days. A wettable powder prepared according to Formulation Example 2 was diluted with water to a seedling seedling having four true leaves developed so that the active ingredient concentration would be 500 ppm, and 20 m1 per pot Sprayed. After air-drying, a spore suspension of apple scab (Venturis inaequalis) was spray-inoculated and immediately placed in a moist chamber at 22 ° C for 48 hours. Thereafter, apple seedlings were transferred into a greenhouse to cause disease, and 14 days after inoculation, the diseased area of the top two leaves at the time of inoculation was investigated and evaluated according to the criteria in Table 59. The results are shown in Tables 62 to 66.

(Table 62.) Compound number Evaluation

1 1 1 A

1 1 2 A

1 3 A

1 1 4 A

1-6 A

1 7 A

1-10 A

1-1 1 A

1-1 2 A

1-13 A

1-14 A

1-1 7 A

1-18 A

1-33 A

1-34 A

1-35 A

1 -40 A

1 -4 1 A

1 -42 A

1 -72 A

1-1 03 A

1-1 1 7 A

1-1 1 8 A

1-1 1 9 A

1-1 20 A

1-1 22 A

1-1 25 A

1-1 37 A

1-146 B

1-1 63 A

1-1 65 A

1-1 661 B (Table 63) Compound number Evaluation

1-1 68 A

1-1 78 A

1-1 92 A

1-1 93 A

1-1 94 A

1-1 95 A

1-1 98 A

1-20 1 A

1-202 A

1-262 B

1-264 A

1-266 A

1-275 A

1-277 A

1-298 A

2-1 7 A

2-2 1 A

2- 22 A

2- 65 B

2- 9 1 A

2—95 A

2- 97 A

2-98 A

2- 102 A

2- 1 06 A

2- 1 07 A

2- 1 09 A

2-1 1 0 A

2- 1 1 1 A

2-1 1 2 A

2-1 1 3 A

2- 1 14 A (Table 64) Compound number Evaluation

2-1 2 1 A

2-1 22 A

2-1 23 A

2- 1 24 A

2-1 26 A

2-1 30 A

2-1 64 A

2-1 66 A

2- 1 83 A

2-1 84 A

2- 1 85 A

2- 1 86 A

2-1 87 A

2-1 88 A

2-1 89 A

2- 1 90 A

2-1 9 1 A

2-1 92 A

2-1 93 A

2-1 94 A

2-20 1 A

2-202 A

2- 203 A

2- 204 A

2- 205 A

2- 206 A

2- 207 A

2-208 A

2- 2 15 A

2- 2 16 A

2-220 A

2- 223 A (Table 65) Compound evaluation

2-2 2 6 B

2-244 A

2-24 5 A

2-24 6 A

2-24 7 A

2-24 8 A

2-24 9 A

2-2 5 1 A

2-2 5 7 A

2-2 6 6 A

2-2 6 8 A

2-277 A

2-2 80 A

2-2 84 A

2-2 8 8 A

2-290 A

2-2 9 9 A

2-3 0 0 A

2-3 28 B

2-3 3 1 A

2-3 3 2 A

2-3 3 3 A

2-3 34 A

2-34 3 A

2-344 A

2-34 6 A

2-3 6 5 A

2-4 1 2 A

2—44 8 A

2-4 5 0 A

2-4 5 1 B

2-4 5 3 A (Table 66)

Test Example 3 Wheat powdery mildew prevention effect test

Nine wheat seeds (variety: Norin 61) are sown in a 9 cm X 9 cm polyvinyl chloride pot, grown in a greenhouse for 8 days, and wettable powder prepared according to Formulation Example 2 is used as the active ingredient concentration. Was diluted to 500 ppm with water, and sprayed with 10 ml per pot. After air drying, spores of wheat powdery mildew (Erysiphe graminis) were inoculated and placed in a greenhouse at 25 to 30 ° C. Ten days after the inoculation, the diseased area of the first leaf in the whole pot was investigated and evaluated according to the criteria shown in Table 59. The results are shown in Tables 67 to 71. (Table 67) Compound number evaluation

1-1 A

1 1 2 A

1 3 A

1 1 4 B

1-6 A

1 7 A

1-10 A

1-1 1 A

1-1 2 A

1-13 A

1-14 B

1-1 7 B

1-18 A

1-33 A

1-34 A

1-35 A

1 -40 A

1 -4 1 A

1 -42 B

1 -72 A

1-1 1 8 A

1-1 1 9 A

1-1 20 A

1-122 A

1-1 25 A

1-146 B

1-148 B

1-1 50 B

1-1 63 A

1-1 65 B

1-1 66 B

1-1 68 A V ε 2 ΐ-ό

V zz \ -z

V \ z \ -z

V 1 ΐ— S

V 8 ΐ ΐ-2 a S ΐ I-2 a I I ΐ-2 a 0 I Τ-2

V 6 0 ΐ-2

V i 0 I-S

V 9 0 1-2

V S 0

V 8 6-2

V L 6-Z

V S 6-S

V 1 6-2 a zz-z a I s-s e L l-Z

V ΐ 一 Z

V L l Z-\

V L Z ~ I

V 9 9 S-ΐ

V P 9 Z ~ I

V 2 0 2-ΐ

V ΐ 0 S-ΐ

V 8 6 ΐ

V 9 6 ΐ-ΐ

V t 6 ΐ a S 6 ΐ-ΐ

V S 6 ΐ-ΐ

V 8 Ζ ΐ-翻翻

(8 9 Halla)

T6

C. £ 0 / 86df / 13d Z.ieOI / 66 ΟΛ \ (Table 69) Compound number Evaluation

2-1 26 B

2-1 64 A

2-1 66 A

2- 1 83 B

2- 1 84 B

2- 1 85 B

2-1 86 B

2- 1 87 A

2- 1 88 A

2-1 89 A

2- 1 90 A

2-1 9 1 A

2-1 92 B

2- 1 93 A

2- 1 94 A

2- 20 1 A

2- 202 B

2-203 A

2- 204 A

2- 205 A

2- 206 B

2- 207 A

2- 208 A

2- 21 5 B

2-2 1 6 B

2- 220 B

2-223 B

2- 244 B

2-245 A

2- 246 B

2-247 A

2-249 A (Table 70) Compound number Evaluation

2-25 1 B

2-266 A

2- 268 B

2-277 A

2-280 A

2- 284 A

2-288 A

2- 290 B

2-299 A

2-300 A

2-328 B

2-33 1 B

2-332 B

2- 333 B

2-334 B

2- 343 B

2-346 A

2-365 B

2 -4 1 2 A

2-448 A

2 -450 A

2-453 A

2 -455 B

2-46 1 A

2-465 A

2- 55 1 B

3 1 1 B

3-5 B

3-6 A

3 -7 A

3-16 A

3-1 7 A (Table 7 1) I-1 Judgment No. Evaluation ~ 18 A

3-2 1 B

3-26 B

3-28 B

3-30 B

3-32 B

B

/ 1 R

B

3—80 A

3—1 0 1 B

3-1 05 B

3-1 07 B

4-22 A

4-1 99 A

4-20 1 B

6 1 1 B

Test Example 4 Rice Blast Prevention Effect Test

15 seeds of rice seeds (variety: Aichi Asahi ';) were sown in a clay pot with a diameter of 7 cm and grown in a greenhouse for 2 to 3 weeks. The wettable powder prepared in the same manner was diluted with water so that the active ingredient concentration became 500 ppm, and sprayed 10 ml per pot.After air-drying, the conidia of rice blast fungus (Pyricularia oryzae.) Were suspended. The suspension was spray-inoculated and immediately placed in 25 wet chambers for 24 hours, and then transferred to a greenhouse, and 5 days after the inoculation, the number of lesions on the fourth leaf was examined. The evaluation was made based on the criteria of 72. The results are shown in Tables 73 to 75.

(Equation 1) Number of lesions in the treatment area

Control value (%) = (1) X 100

Lesion count in untreated area

(Table 7 2) Evaluation control

A 100% control value

B 100% to 80.0% or more

C 80.0% to less than 50.0%

D 50.0 Control value less than 0%

(Table 73) Compound number Evaluation

1 1 1 A

1 1 2 A

1 3 B

1-6 A

1-10 A

1-1 2 A

1-1 3 B

1-14 B

1-1 7 B

1-1 8 B

1-33 B

1-34 B

1-1 1 8 B

1-1 20 B

1-1 25 B

1-146 B

1-147 B

1-148 B

1-1 50 B

1-1 63 A

1-1 65 A

1-1 66 B

1-1 68 B

1-1 78 A

1-188 B

1-1 92 B

1-1 93 B

1-1 94 B

1-1 95 B

1-1 98 B

1-20 1 B

1-202 B 9f

(Table 74) Compound number

R

1 _ 9 7 A

1

2-1 7 B

2-97 B

2- 102 B

2- 1 06 A

9-1 09 B

2-1 1 0

9-1 1 1 A

9-1 1 R

9 1 1 A

2-1 14 B

2- 1 2 1 B

2-1 64 B

2-1 66 A

2-1 83 A

2-1 84 A

2-1 85 B

2-1 86 A

-1 7 R

2-1 88 A

2- 1 89 B

2- 1 90 A

2- 1 92 B

2- 1 93 A

2-1 94 B

2- 1 96 B

2- 20 1 B

2- 202 B

2-203 B

2-204 B

(9

86

£. £ 0 / 86df / XDd [.IC0I / 66 O Test Example 5 Test for prevention of gray mold on cucumber

Nine cucumber seeds (variety: Sagami Hanjiro) were sowed in each 9 cm X 9 cm PVC pot and cultivated in a greenhouse for 7 days. A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm with an active ingredient, and then sprayed with 10 ml per pot of a cucumber seedling having cotyledons developed. After air-drying, the mycelium of Botrytis cinerea was spray-inoculated with a spray of mycelia gray mold and immediately placed in a moist chamber. After 3 days from the inoculation, the diseased area of the entire pot was investigated and evaluated according to the criteria in Table 59. The results are shown in Tables 76 to 7.

(Table 76) Compound 1 ι_ι Compound No. 1 J evaluation

1 -4 A

1-1 1 B

1-1 2 A

1-35 B

1 -42 B

1-298 A

2- 65 B

2- 1 1 1 B

2-1 22 A

2- 1 89 B

2- 1 90 A

2-1 9 1 A

2- 1 93 A

2- 204 B

2-205 A

2- 207 A

2- 21 5 B

2-2 1 6 B

2- 226 A

2- 246 B

2- 247 B

2- 248 A

2- 249 B

2- 257 B

2- 268 B

2- 288 B

2- 300 A

2-33 1 A

2-332 B

2- 334 A

2- 343 B

2- 346 B (Table 77)

Test example 6 Rice sheath blight prevention effect test

Fifteen rice seeds (variety: Kinnan style) were sown in unglazed pots with a diameter of 7 cm and cultivated in a greenhouse for 4 to 5 weeks. The hydration agent prepared according to Formulation Example 2 was diluted with water so that the active ingredient concentration became 500 ppm, and the rice seedling with the developed fifth leaf was sprayed with 10 m 1 per pot. After air-drying, Rhizoctonia solani, which was cultured in a fir-garrafuma medium, was inoculated into the root of the strain and immediately placed in a humidity chamber at 28 ° C. Six days later, the height of the lesion formed on the rice leaf sheath was measured, and the control value was calculated according to Equation 2, and evaluated based on the criteria in Table 72. The results are shown in Tables 78 to 79.

(Equation 2) Lesion height in treatment area

Control value (%) = (1 100

Lesion height in untreated area (Table 78) Compound evaluation

1-10 B

1 1 1 1 B

1-1 3 B

1-14 B

1-34 A

1-35 B

1-1 1 9 B

1-1 20 A

1-1 22 B

1-1 25 B

1-1 37 B

1-1 78 B

2-98 B

2-102 A

2-1 07 B

2-1 09 B

2-1 1 0 B

2— 1 1 1 B

2-1 1 2 B

2- 1 1 3 B

2-1 14 A

2- 1 21 A

2- 1 22 B

2-1 26 B

2- 1 66 A

2-1 90 B

2- 1 94 B

2-1 96 B

2- 20 1 B

2-205 A

2-206 B

2- 244 B (Table 79) I 1 item list "H No.

2-247 Β

2-249 Β

2-25 1 Β

2-277 Β

2-4 1 2 Β

2 -450 Β

3-6 Β

3-1 6 Β

3-2 1 Β

Claims

The scope of the claims

1. General formula [I]

(Wherein X is a halogen atom, (C; [-C _6] ) alkyl group, (C i —C s) alkoxy group, (丄 C ₄ ) haloalkyl group or (C i —C 4) haloalkoxy group And n represents 0 or an integer of 1 to 4, R 1 represents a (C; —C ₆ ) alkyl group,

(C 2 -C 6) alkenyl, (C 2 -C ₆ ) alkynyl, (C ₃ -C ₆ ) cycloalkyl or (C i -C) haloalkyl, R ² is a hydrogen atom,

(C丄- C ₆₎ alkyl groups, (C 2- C ₆₎ alkenyl, (C ₂ one C 6) al Kiniru group, (C 1 - C 4) alkoxy groups, (C - C 6) alkoxy (C E - C ₄₎ alkyl group, (C; [- C 6 ) alkylthio (C - C i) alkyl groups,

(C 1 -C 4) haloalkyl group, (C i -C 6) alkylcarbonyl group, phenylcarbonyl group, (C ₄ -C ₄ ) alkoxycarbonyl group or aryl (C 1 -C 4) alkyl group May be substituted with a halogen atom, a (C 丄 -C ₃ ) alkyl group, or a (C: [-C ₃ ) alkoxy group. A represents an optionally branched (C i—C?) Alkylene group; G represents an oxygen atom, a sulfur atom or a group —NR— [R ³ represents a hydrogen atom or (C i—C ₄ ) Represents an alkyl group. ] And Q is a general formula

Wherein Y is a halogen atom, nitro, cyano, hydroxy, (C 1 -C 6) alkyl, (C 2 -C ₆ ) alkenyl, (C 2 -C ₆ ) alkynyl, (C 3- C ₆₎ cycloalkyl group, (C 3- C 6) cycloalkyl Le (C one C 4) alkyl group, (C one C ₆₎ alkoxy _{groups, (C; -? C 6} ) 7 Rukeniruokishi group, (C 2 one C ₆₎ Arukiniruokishi group, (C 3- C g) cycloalkyl alkoxy, (C丄- C ₆₎ alkylthio group, (C丄one C ₆₎ Arukirusurufu Iniru group, (C丄—C ₆ ) alkylsulfonyl group, (C i—C) alkoxy

(C 1 -C 4) alkyl group, (C i-C ^) alkylthio (C i-C 4) alkyl group, (C 1 -C 4) haloalkyl group, (C 1 -C 4) haloalkoxy group,

(C1-C4) haloalkylthio group, (Ci-C4) haloalkylsulfinyl group, (C-C4) haloalkylsulfonyl group, (C1-C4) alkylcarbonyl group, (C1-C4) ) An alkoxycarbonyl group, a group C〇NR ⁴ R [R ⁴ and R ^{それぞれ} are the same or different and each ^represents a hydrogen atom or a (C i -C ₄ ) alkyl group. ], Amino group, mono (C 1 -C 4) alkylamino group, di (C 1 -C 4) alkylamino group,, (C 1 -C 4) alkylcarbonylamino group, aryl group

[Said group halogen atom, (C i- C ₄₎ alkyl group or - may be substituted by (C C ₄₎ an alkoxy group. ], Aryloxy group [the group is a halogen atom,

(C -! C ₄₎ alkyl or (C i-C4) may be substituted with an alkoxy group. ], Aryl (C 1 -C 4) alkoxy group [The group may be substituted with a halogen atom, a (C 1 -C 4) alkyl group or a (C 1 -C 4) alkoxy group. Or an adjacent substituent may be bonded to form a methylenedioxy group, and m represents 0 or an integer of 1 to 5. And a biarylalkylene carbamic acid derivative represented by the formula:

2. A fungicide for agricultural and horticultural use, comprising the biarylalkylenecarbamic acid derivative according to claim 1 as an active ingredient.